#------------------------------------------------------------------------------
#$Date: 2019-11-10 06:14:20 +0200 (Sun, 10 Nov 2019) $
#$Revision: 225683 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/15/71/7157193.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_7157193
loop_
_publ_author_name
'Song, Bo'
'Wang, Mengdan'
'Xu, Murong'
'Kong, Lingkai'
'Xie, Huihui'
'Wang, Cheng-Yu'
'LI, Yanzhong'
_publ_section_title
;
 Controllable Synthesis of Pyrido[2,3-b]indol-4-ones or
 Indolo[3,2-b]quinolines via Formal Intramolecular C(sp2)-H
 Functionalization
;
_journal_name_full               'Organic & Biomolecular Chemistry'
_journal_paper_doi               10.1039/C9OB02108F
_journal_year                    2019
_chemical_formula_sum            'C24 H18 N2 O'
_chemical_formula_weight         350.40
_space_group_crystal_system      orthorhombic
_space_group_IT_number           57
_space_group_name_Hall           '-P 2c 2b'
_space_group_name_H-M_alt        'P b c m'
_atom_sites_solution_hydrogens   geom
_audit_block_doi                 10.5517/ccdc.csd.cc237srx
_audit_creation_method           SHELXL-2013
_audit_update_record
;
2019-07-29 deposited with the CCDC.	2019-11-08 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   9.9294(3)
_cell_length_b                   22.8248(8)
_cell_length_c                   8.0346(3)
_cell_measurement_reflns_used    9847
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      54.583
_cell_measurement_theta_min      4.473
_cell_volume                     1820.93(11)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.969
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0633
_diffrn_reflns_av_unetI/netI     0.0178
_diffrn_reflns_Laue_measured_fraction_full 0.969
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       27
_diffrn_reflns_limit_k_min       -27
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            44964
_diffrn_reflns_point_group_measured_fraction_full 0.969
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.000
_diffrn_reflns_theta_min         2.237
_exptl_absorpt_coefficient_mu    0.079
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.5617
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.278
_exptl_crystal_description       prismatic
_exptl_crystal_F_000             736
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.150
_exptl_crystal_size_min          0.100
_refine_diff_density_max         0.190
_refine_diff_density_min         -0.128
_refine_diff_density_rms         0.044
_refine_ls_extinction_coef       0.126(17)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.050
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     153
_refine_ls_number_reflns         1722
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.050
_refine_ls_R_factor_all          0.0574
_refine_ls_R_factor_gt           0.0510
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.1076P)²+0.2445P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1542
_refine_ls_wR_factor_ref         0.1661
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1489
_reflns_number_total             1722
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            c9ob02108f2.cif
_cod_data_source_block           d8v18241
_cod_database_code               7157193
_shelx_space_group_comment
; 
The symmetry employed for this shelxl refinement is uniquely defined 
by the following loop, which should always be used as a source of 
symmetry information in preference to the above space-group names. 
They are only intended as comments. 
;
_shelx_estimated_absorpt_t_min   0.984
_shelx_estimated_absorpt_t_max   0.992
_shelxl_version_number           2013-4
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, z+1/2'
'x, -y+1/2, -z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, y, -z-1/2'
'-x, 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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
O1 O 0.43244(16) 0.85047(6) 0.2500 0.0688(5) Uani 1 2 d S T P
N1 N 0.77023(17) 0.71049(8) 0.2500 0.0681(6) Uani 1 2 d S T P
N2 N 0.53707(15) 0.67532(7) 0.2500 0.0545(5) Uani 1 2 d S T P
C1 C 0.8286(2) 0.76608(10) 0.2500 0.0720(7) Uani 1 2 d S T P
C2 C 0.9647(3) 0.78057(13) 0.2500 0.1050(12) Uani 1 2 d S T P
H2 H 1.0308 0.7517 0.2500 0.126 Uiso 1 2 calc R U P
C3 C 0.9976(3) 0.83859(14) 0.2500 0.1268(16) Uani 1 2 d S T P
H3 H 1.0879 0.8494 0.2500 0.152 Uiso 1 2 calc R U P
C4 C 0.8997(3) 0.88153(13) 0.2500 0.1117(12) Uani 1 2 d S T P
H4 H 0.9254 0.9207 0.2500 0.134 Uiso 1 2 calc R U P
C5 C 0.7645(3) 0.86748(11) 0.2500 0.0793(8) Uani 1 2 d S T P
H5 H 0.6993 0.8967 0.2500 0.095 Uiso 1 2 calc R U P
C6 C 0.7278(2) 0.80871(10) 0.2500 0.0614(6) Uani 1 2 d S T P
C7 C 0.6018(2) 0.77784(8) 0.2500 0.0524(6) Uani 1 2 d S T P
C8 C 0.6333(2) 0.71846(8) 0.2500 0.0535(6) Uani 1 2 d S T P
C9 C 0.40276(19) 0.69297(9) 0.2500 0.0535(5) Uani 1 2 d S T P
C10 C 0.36981(19) 0.75037(9) 0.2500 0.0617(6) Uani 1 2 d S T P
H10 H 0.2788 0.7601 0.2500 0.074 Uiso 1 2 calc R U P
C11 C 0.4658(2) 0.79752(8) 0.2500 0.0530(5) Uani 1 2 d S T P
C12 C 0.8532(3) 0.65792(11) 0.2500 0.0964(11) Uani 1 2 d S T P
H12A H 0.8663 0.6448 0.3624 0.145 Uiso 0.5 1 calc R U P
H12B H 0.9390 0.6665 0.2006 0.145 Uiso 0.5 1 calc R U P
H12C H 0.8092 0.6277 0.1870 0.145 Uiso 0.5 1 calc R U P
C13 C 0.57191(19) 0.61383(8) 0.2500 0.0525(5) Uani 1 2 d S T P
C14 C 0.5881(2) 0.58527(8) 0.3968(2) 0.0836(6) Uani 1 1 d . . .
H14 H 0.5713 0.6043 0.4971 0.100 Uiso 1 1 calc R U .
C15 C 0.6299(2) 0.52747(9) 0.3951(3) 0.1017(8) Uani 1 1 d . . .
H15 H 0.6432 0.5079 0.4953 0.122 Uiso 1 1 calc R U .
C16 C 0.6516(3) 0.49909(11) 0.2500 0.0900(9) Uani 1 2 d S T P
H16 H 0.6812 0.4604 0.2500 0.108 Uiso 1 2 calc R U P
C17 C 0.2997(2) 0.64548(9) 0.2500 0.0574(6) Uani 1 2 d S T P
C18 C 0.2495(2) 0.62377(9) 0.3965(3) 0.0887(7) Uani 1 1 d . . .
H18 H 0.2811 0.6383 0.4973 0.106 Uiso 1 1 calc R U .
C19 C 0.1520(2) 0.58042(9) 0.3952(3) 0.1002(8) Uani 1 1 d . . .
H19 H 0.1198 0.5656 0.4954 0.120 Uiso 1 1 calc R U .
C20 C 0.1031(2) 0.55932(10) 0.2500 0.0838(9) Uani 1 2 d S T P
H20 H 0.0365 0.5306 0.2500 0.101 Uiso 1 2 calc R U P
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
C8 N1 C1 106.92(17) . .
C8 N1 C12 132.11(19) . .
C1 N1 C12 120.96(19) . .
C8 N2 C9 117.33(16) . .
C8 N2 C13 122.01(16) . .
C9 N2 C13 120.66(16) . .
C2 C1 N1 128.3(2) . .
C2 C1 C6 122.1(2) . .
N1 C1 C6 109.63(19) . .
C3 C2 C1 117.6(3) . .
C3 C2 H2 121.2 . .
C1 C2 H2 121.2 . .
C2 C3 C4 121.3(3) . .
C2 C3 H3 119.3 . .
C4 C3 H3 119.3 . .
C5 C4 C3 121.3(3) . .
C5 C4 H4 119.3 . .
C3 C4 H4 119.3 . .
C4 C5 C6 118.6(2) . .
C4 C5 H5 120.7 . .
C6 C5 H5 120.7 . .
C5 C6 C1 119.0(2) . .
C5 C6 C7 134.6(2) . .
C1 C6 C7 106.43(19) . .
C8 C7 C11 121.43(18) . .
C8 C7 C6 106.36(18) . .
C11 C7 C6 132.21(18) . .
N1 C8 N2 126.52(17) . .
N1 C8 C7 110.65(18) . .
N2 C8 C7 122.83(18) . .
C10 C9 N2 120.84(19) . .
C10 C9 C17 122.61(18) . .
N2 C9 C17 116.55(17) . .
C9 C10 C11 124.44(18) . .
C9 C10 H10 117.8 . .
C11 C10 H10 117.8 . .
O1 C11 C7 123.74(19) . .
O1 C11 C10 123.13(19) . .
C7 C11 C10 113.13(17) . .
N1 C12 H12A 109.5 . .
N1 C12 H12B 109.5 . .
H12A C12 H12B 109.5 . .
N1 C12 H12C 109.5 . .
H12A C12 H12C 109.5 . .
H12B C12 H12C 109.5 . .
C14 C13 C14 120.7(2) 6_556 .
C14 C13 N2 119.64(10) 6_556 .
C14 C13 N2 119.64(10) . .
C13 C14 C15 119.01(18) . .
C13 C14 H14 120.5 . .
C15 C14 H14 120.5 . .
C16 C15 C14 120.91(19) . .
C16 C15 H15 119.5 . .
C14 C15 H15 119.5 . .
C15 C16 C15 119.3(2) 6_556 .
C15 C16 H16 120.3 6_556 .
C15 C16 H16 120.3 . .
C18 C17 C18 118.3(2) 6_556 .
C18 C17 C9 120.83(11) 6_556 .
C18 C17 C9 120.83(11) . .
C17 C18 C19 120.4(2) . .
C17 C18 H18 119.8 . .
C19 C18 H18 119.8 . .
C20 C19 C18 120.8(2) . .
C20 C19 H19 119.6 . .
C18 C19 H19 119.6 . .
C19 C20 C19 119.2(2) . 6_556
C19 C20 H20 120.4 . .
C19 C20 H20 120.4 6_556 .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
O1 C11 1.253(2) .
N1 C8 1.371(3) .
N1 C1 1.395(3) .
N1 C12 1.456(3) .
N2 C8 1.372(3) .
N2 C9 1.393(2) .
N2 C13 1.445(2) .
C1 C2 1.391(3) .
C1 C6 1.396(3) .
C2 C3 1.364(4) .
C2 H2 0.9300 .
C3 C4 1.381(5) .
C3 H3 0.9300 .
C4 C5 1.381(4) .
C4 H4 0.9300 .
C5 C6 1.390(3) .
C5 H5 0.9300 .
C6 C7 1.436(3) .
C7 C8 1.391(3) .
C7 C11 1.423(3) .
C9 C10 1.350(3) .
C9 C17 1.491(3) .
C10 C11 1.438(3) .
C10 H10 0.9300 .
C12 H12A 0.9600 .
C12 H12B 0.9600 .
C12 H12C 0.9600 .
C13 C14 1.357(2) 6_556
C13 C14 1.357(2) .
C14 C15 1.383(3) .
C14 H14 0.9300 .
C15 C16 1.351(3) .
C15 H15 0.9300 .
C16 C15 1.351(3) 6_556
C16 H16 0.9300 .
C17 C18 1.371(2) 6_556
C17 C18 1.371(2) .
C18 C19 1.384(3) .
C18 H18 0.9300 .
C19 C20 1.353(3) .
C19 H19 0.9300 .
C20 C19 1.353(3) 6_556
C20 H20 0.9300 .
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_4
C8 N1 C1 C2 180.0 . .
C12 N1 C1 C2 0.0 . .
C8 N1 C1 C6 0.0 . .
C12 N1 C1 C6 180.0 . .
N1 C1 C2 C3 180.0 . .
C6 C1 C2 C3 0.0 . .
C1 C2 C3 C4 0.0 . .
C2 C3 C4 C5 0.0 . .
C3 C4 C5 C6 0.0 . .
C4 C5 C6 C1 0.0 . .
C4 C5 C6 C7 180.0 . .
C2 C1 C6 C5 0.0 . .
N1 C1 C6 C5 180.0 . .
C2 C1 C6 C7 180.0 . .
N1 C1 C6 C7 0.0 . .
C5 C6 C7 C8 180.0 . .
C1 C6 C7 C8 0.0 . .
C5 C6 C7 C11 0.0 . .
C1 C6 C7 C11 180.0 . .
C1 N1 C8 N2 180.0 . .
C12 N1 C8 N2 0.0 . .
C1 N1 C8 C7 0.0 . .
C12 N1 C8 C7 180.0 . .
C9 N2 C8 N1 180.0 . .
C13 N2 C8 N1 0.0 . .
C9 N2 C8 C7 0.0 . .
C13 N2 C8 C7 180.0 . .
C11 C7 C8 N1 180.0 . .
C6 C7 C8 N1 0.0 . .
C11 C7 C8 N2 0.0 . .
C6 C7 C8 N2 180.0 . .
C8 N2 C9 C10 0.0 . .
C13 N2 C9 C10 180.0 . .
C8 N2 C9 C17 180.0 . .
C13 N2 C9 C17 0.0 . .
N2 C9 C10 C11 0.0 . .
C17 C9 C10 C11 180.0 . .
C8 C7 C11 O1 180.0 . .
C6 C7 C11 O1 0.0 . .
C8 C7 C11 C10 0.0 . .
C6 C7 C11 C10 180.0 . .
C9 C10 C11 O1 180.0 . .
C9 C10 C11 C7 0.0 . .
C8 N2 C13 C14 -90.02(18) . 6_556
C9 N2 C13 C14 89.98(18) . 6_556
C8 N2 C13 C14 90.02(18) . .
C9 N2 C13 C14 -89.98(18) . .
C14 C13 C14 C15 4.2(4) 6_556 .
N2 C13 C14 C15 -175.9(2) . .
C13 C14 C15 C16 -1.5(4) . .
C14 C15 C16 C15 -1.1(5) . 6_556
C10 C9 C17 C18 88.92(19) . 6_556
N2 C9 C17 C18 -91.08(19) . 6_556
C10 C9 C17 C18 -88.92(19) . .
N2 C9 C17 C18 91.08(19) . .
C18 C17 C18 C19 0.9(4) 6_556 .
C9 C17 C18 C19 178.84(19) . .
C17 C18 C19 C20 -1.0(4) . .
C18 C19 C20 C19 1.1(4) . 6_556
