#------------------------------------------------------------------------------
#$Date: 2016-02-13 14:50:18 +0200 (Sat, 13 Feb 2016) $
#$Revision: 176428 $
#$URL: svn://www.crystallography.net/cod/cif/7/11/86/7118668.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_7118668
loop_
_publ_author_name
'Nagaraju Barsu'
'Malay Sen'
'J. Richard Premkumar'
'Basker Sundararaju'
_publ_section_title
;
 Cobalt(III) catalyzed C-8 selective C-H and C-O coupling of quinoline
 N-oxide with internal alkynes via C-H activation and oxygen atom transfer
;
_journal_name_full               Chem.Commun.
_journal_page_first              1338
_journal_volume                  52
_journal_year                    2016
_chemical_formula_sum            'C29 H21 N O'
_chemical_formula_weight         399.47
_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
_audit_update_record
;
2015-10-09 deposited with the CCDC.
2015-11-23 downloaded from the CCDC.
;
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   9.002(2)
_cell_length_b                   13.225(3)
_cell_length_c                   17.293(4)
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      24.33
_cell_measurement_theta_min      2.36
_cell_volume                     2058.8(8)
_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-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and 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  0.0547
_diffrn_reflns_av_sigmaI/netI    0.0607
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            10700
_diffrn_reflns_theta_full        25.38
_diffrn_reflns_theta_max         25.38
_diffrn_reflns_theta_min         1.94
_exptl_absorpt_coefficient_mu    0.077
_exptl_absorpt_correction_T_max  0.9900
_exptl_absorpt_correction_T_min  0.9847
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            Colourless
_exptl_crystal_density_diffrn    1.289
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Needle
_exptl_crystal_F_000             840
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.13
_refine_diff_density_max         0.187
_refine_diff_density_min         -0.179
_refine_diff_density_rms         0.044
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   5(2)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.070
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     280
_refine_ls_number_reflns         3767
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.070
_refine_ls_R_factor_all          0.0624
_refine_ls_R_factor_gt           0.0451
_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)+(0.0478P)²+0.2935P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0966
_refine_ls_wR_factor_ref         0.1162
_reflns_number_gt                3065
_reflns_number_total             3767
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c5cc08736h2.cif
_cod_data_source_block           N_oxide
_cod_original_cell_volume        2058.7(8)
_cod_original_sg_symbol_H-M      P2(1)2(1)2(1)
_cod_database_code               7118668
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -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
O1 O 0.2251(2) 0.05923(13) 0.53655(10) 0.0321(5) Uani 1 1 d . . .
N2 N 0.1216(2) 0.17299(15) 0.36494(12) 0.0256(5) Uani 1 1 d . . .
C3 C 0.0355(3) -0.13489(19) 0.34280(16) 0.0311(6) Uani 1 1 d . . .
H3A H 0.0147 -0.2051 0.3387 0.037 Uiso 1 1 calc R . .
C4 C 0.0947(3) 0.07131(18) 0.35689(14) 0.0237(6) Uani 1 1 d . . .
C5 C 0.1887(3) 0.2203(2) 0.30779(14) 0.0252(6) Uani 1 1 d . . .
H5A H 0.2051 0.2909 0.3133 0.030 Uiso 1 1 calc R . .
C6 C 0.1057(3) -0.0867(2) 0.28408(15) 0.0311(6) Uani 1 1 d . . .
H6A H 0.1341 -0.1236 0.2393 0.037 Uiso 1 1 calc R . .
C7 C 0.0217(3) 0.01924(18) 0.41802(14) 0.0252(6) Uani 1 1 d . . .
C8 C 0.1201(3) 0.39276(19) 0.65946(15) 0.0294(6) Uani 1 1 d . . .
H8A H 0.1229 0.4545 0.6874 0.035 Uiso 1 1 calc R . .
C9 C -0.0103(3) 0.27684(18) 0.57623(14) 0.0248(6) Uani 1 1 d . . .
H9A H -0.0970 0.2593 0.5480 0.030 Uiso 1 1 calc R . .
C10 C 0.2368(3) 0.23886(18) 0.61972(13) 0.0237(6) Uani 1 1 d . . .
H10A H 0.3215 0.1960 0.6200 0.028 Uiso 1 1 calc R . .
C11 C -0.0045(3) 0.36718(19) 0.61628(14) 0.0271(6) Uani 1 1 d . . .
H11A H -0.0866 0.4122 0.6143 0.033 Uiso 1 1 calc R . .
C12 C -0.1313(3) 0.03144(18) 0.54324(13) 0.0234(6) Uani 1 1 d . . .
C13 C -0.1905(3) -0.0932(2) 0.63979(15) 0.0315(7) Uani 1 1 d . . .
H13A H -0.1598 -0.1474 0.6721 0.038 Uiso 1 1 calc R . .
C14 C 0.1122(3) 0.21090(18) 0.57726(14) 0.0235(6) Uani 1 1 d . . .
C15 C 0.1157(3) 0.11332(19) 0.53338(14) 0.0240(6) Uani 1 1 d . . .
C16 C -0.0219(3) 0.08153(18) 0.48840(14) 0.0235(6) Uani 1 1 d . . .
H16A H -0.0700 0.1447 0.4689 0.028 Uiso 1 1 calc R . .
C17 C 0.2384(3) 0.1738(2) 0.23849(13) 0.0251(6) Uani 1 1 d . . .
C18 C -0.0071(3) -0.08159(18) 0.41003(15) 0.0283(6) Uani 1 1 d . . .
H18A H -0.0567 -0.1166 0.4505 0.034 Uiso 1 1 calc R . .
C19 C -0.0888(3) -0.04668(18) 0.59200(14) 0.0269(6) Uani 1 1 d . . .
H19A H 0.0117 -0.0684 0.5924 0.032 Uiso 1 1 calc R . .
C20 C 0.1372(3) 0.01760(19) 0.28884(14) 0.0259(6) Uani 1 1 d . . .
C21 C 0.3183(3) 0.23409(19) 0.17910(15) 0.0289(7) Uani 1 1 d . . .
C22 C -0.3810(3) 0.01696(19) 0.59295(14) 0.0301(6) Uani 1 1 d . . .
H22A H -0.4814 0.0391 0.5931 0.036 Uiso 1 1 calc R . .
C23 C -0.3371(3) -0.06155(19) 0.64099(15) 0.0290(6) Uani 1 1 d . . .
H23A H -0.4069 -0.0932 0.6743 0.035 Uiso 1 1 calc R . .
C24 C 0.4303(3) 0.30096(19) 0.20130(17) 0.0336(7) Uani 1 1 d . . .
H24A H 0.4535 0.3090 0.2545 0.040 Uiso 1 1 calc R . .
C25 C 0.2091(3) 0.0728(2) 0.22955(14) 0.0278(6) Uani 1 1 d . . .
H25A H 0.2373 0.0395 0.1831 0.033 Uiso 1 1 calc R . .
C26 C -0.2783(3) 0.06310(19) 0.54476(14) 0.0262(6) Uani 1 1 d . . .
H26A H -0.3089 0.1172 0.5123 0.031 Uiso 1 1 calc R . .
C27 C 0.2850(3) 0.2240(2) 0.10050(15) 0.0371(7) Uani 1 1 d . . .
H27A H 0.2098 0.1782 0.0844 0.045 Uiso 1 1 calc R . .
C28 C 0.2396(3) 0.3277(2) 0.66133(14) 0.0265(6) Uani 1 1 d . . .
H28A H 0.3245 0.3442 0.6915 0.032 Uiso 1 1 calc R . .
C29 C 0.4737(4) 0.3460(2) 0.06880(19) 0.0470(9) Uani 1 1 d . . .
H29A H 0.5269 0.3840 0.0313 0.056 Uiso 1 1 calc R . .
C30 C 0.5080(4) 0.3557(2) 0.14623(19) 0.0429(8) Uani 1 1 d . . .
H30A H 0.5852 0.4002 0.1619 0.052 Uiso 1 1 calc R . .
C31 C 0.3617(4) 0.2807(2) 0.04582(17) 0.0447(8) Uani 1 1 d . . .
H31A H 0.3373 0.2747 -0.0074 0.054 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
C5 N2 C4 118.0(2) . .
C6 C3 C18 120.6(2) . .
N2 C4 C7 118.7(2) . .
N2 C4 C20 121.6(2) . .
C7 C4 C20 119.7(2) . .
N2 C5 C17 124.9(2) . .
C3 C6 C20 120.6(2) . .
C18 C7 C4 119.0(2) . .
C18 C7 C16 124.1(2) . .
C4 C7 C16 116.8(2) . .
C28 C8 C11 119.4(2) . .
C11 C9 C14 120.0(2) . .
C28 C10 C14 121.1(2) . .
C9 C11 C8 120.7(2) . .
C19 C12 C26 118.4(2) . .
C19 C12 C16 121.7(2) . .
C26 C12 C16 119.9(2) . .
C19 C13 C23 120.5(2) . .
C10 C14 C9 118.3(2) . .
C10 C14 C15 118.7(2) . .
C9 C14 C15 123.0(2) . .
O1 C15 C14 120.0(2) . .
O1 C15 C16 121.2(2) . .
C14 C15 C16 118.7(2) . .
C12 C16 C7 115.5(2) . .
C12 C16 C15 109.21(19) . .
C7 C16 C15 110.4(2) . .
C25 C17 C5 117.2(2) . .
C25 C17 C21 122.6(2) . .
C5 C17 C21 120.2(2) . .
C7 C18 C3 121.3(3) . .
C13 C19 C12 120.9(3) . .
C6 C20 C25 123.6(2) . .
C6 C20 C4 118.8(2) . .
C25 C20 C4 117.6(2) . .
C24 C21 C27 118.9(3) . .
C24 C21 C17 120.0(2) . .
C27 C21 C17 121.1(3) . .
C26 C22 C23 120.0(3) . .
C13 C23 C22 119.3(3) . .
C30 C24 C21 120.5(3) . .
C17 C25 C20 120.6(2) . .
C22 C26 C12 121.0(2) . .
C31 C27 C21 120.2(3) . .
C8 C28 C10 120.4(2) . .
C30 C29 C31 119.9(3) . .
C29 C30 C24 120.4(3) . .
C29 C31 C27 120.2(3) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
O1 C15 1.218(3) .
N2 C5 1.316(3) .
N2 C4 1.374(3) .
C3 C6 1.355(4) .
C3 C18 1.413(4) .
C4 C7 1.423(3) .
C4 C20 1.427(3) .
C5 C17 1.419(3) .
C6 C20 1.411(4) .
C7 C18 1.366(3) .
C7 C16 1.521(3) .
C8 C28 1.378(4) .
C8 C11 1.390(4) .
C9 C11 1.382(3) .
C9 C14 1.406(4) .
C10 C28 1.378(3) .
C10 C14 1.391(4) .
C12 C19 1.387(3) .
C12 C26 1.388(4) .
C12 C16 1.519(3) .
C13 C19 1.378(4) .
C13 C23 1.385(4) .
C14 C15 1.497(3) .
C15 C16 1.522(4) .
C17 C25 1.370(4) .
C17 C21 1.486(4) .
C20 C25 1.415(4) .
C21 C24 1.396(4) .
C21 C27 1.398(4) .
C22 C26 1.386(4) .
C22 C23 1.387(4) .
C24 C30 1.386(4) .
C27 C31 1.391(4) .
C29 C30 1.380(5) .
C29 C31 1.386(5) .
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_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
C5 N2 C4 C7 -179.7(2) . . . .
C5 N2 C4 C20 -0.2(4) . . . .
C4 N2 C5 C17 -1.3(4) . . . .
C18 C3 C6 C20 -0.2(4) . . . .
N2 C4 C7 C18 179.2(2) . . . .
C20 C4 C7 C18 -0.3(4) . . . .
N2 C4 C7 C16 0.2(3) . . . .
C20 C4 C7 C16 -179.3(2) . . . .
C14 C9 C11 C8 -1.6(4) . . . .
C28 C8 C11 C9 0.8(4) . . . .
C28 C10 C14 C9 1.5(4) . . . .
C28 C10 C14 C15 -179.9(2) . . . .
C11 C9 C14 C10 0.5(4) . . . .
C11 C9 C14 C15 -178.1(2) . . . .
C10 C14 C15 O1 1.5(3) . . . .
C9 C14 C15 O1 -180.0(2) . . . .
C10 C14 C15 C16 178.6(2) . . . .
C9 C14 C15 C16 -2.8(3) . . . .
C19 C12 C16 C7 73.8(3) . . . .
C26 C12 C16 C7 -105.5(3) . . . .
C19 C12 C16 C15 -51.3(3) . . . .
C26 C12 C16 C15 129.3(2) . . . .
C18 C7 C16 C12 -13.3(4) . . . .
C4 C7 C16 C12 165.6(2) . . . .
C18 C7 C16 C15 111.2(3) . . . .
C4 C7 C16 C15 -69.9(3) . . . .
O1 C15 C16 C12 94.9(3) . . . .
C14 C15 C16 C12 -82.2(3) . . . .
O1 C15 C16 C7 -33.1(3) . . . .
C14 C15 C16 C7 149.8(2) . . . .
N2 C5 C17 C25 2.6(4) . . . .
N2 C5 C17 C21 -177.6(2) . . . .
C4 C7 C18 C3 0.6(4) . . . .
C16 C7 C18 C3 179.5(2) . . . .
C6 C3 C18 C7 -0.4(4) . . . .
C23 C13 C19 C12 -1.1(4) . . . .
C26 C12 C19 C13 1.2(4) . . . .
C16 C12 C19 C13 -178.1(2) . . . .
C3 C6 C20 C25 -179.5(3) . . . .
C3 C6 C20 C4 0.5(4) . . . .
N2 C4 C20 C6 -179.7(2) . . . .
C7 C4 C20 C6 -0.2(4) . . . .
N2 C4 C20 C25 0.3(4) . . . .
C7 C4 C20 C25 179.8(2) . . . .
C25 C17 C21 C24 -135.3(3) . . . .
C5 C17 C21 C24 44.8(4) . . . .
C25 C17 C21 C27 43.6(4) . . . .
C5 C17 C21 C27 -136.3(3) . . . .
C19 C13 C23 C22 0.6(4) . . . .
C26 C22 C23 C13 -0.3(4) . . . .
C27 C21 C24 C30 -0.5(4) . . . .
C17 C21 C24 C30 178.4(2) . . . .
C5 C17 C25 C20 -2.3(4) . . . .
C21 C17 C25 C20 177.8(2) . . . .
C6 C20 C25 C17 -178.9(3) . . . .
C4 C20 C25 C17 1.1(4) . . . .
C23 C22 C26 C12 0.5(4) . . . .
C19 C12 C26 C22 -0.9(4) . . . .
C16 C12 C26 C22 178.4(2) . . . .
C24 C21 C27 C31 -0.7(4) . . . .
C17 C21 C27 C31 -179.6(3) . . . .
C11 C8 C28 C10 1.1(4) . . . .
C14 C10 C28 C8 -2.3(4) . . . .
C31 C29 C30 C24 -0.4(4) . . . .
C21 C24 C30 C29 1.1(4) . . . .
C30 C29 C31 C27 -0.8(4) . . . .
C21 C27 C31 C29 1.4(4) . . . .
