#------------------------------------------------------------------------------
#$Date: 2016-02-05 03:25:12 +0200 (Fri, 05 Feb 2016) $
#$Revision: 176201 $
#$URL: svn://www.crystallography.net/cod/cif/7/15/47/7154794.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_7154794
loop_
_publ_author_name
'Li, Lei'
'Wang, Qian'
'Liu, Pei'
'Meng, Hua'
'Kan, Xing-Lan'
'Liu, Qun'
'Zhao, Yu-Long'
_publ_section_title
;
 DBU-mediated metal-free oxidative cyanation of α-amino carbonyl
 compounds: using molecular oxygen as the oxidant.
;
_journal_issue                   1
_journal_name_full               'Organic & biomolecular chemistry'
_journal_page_first              165
_journal_page_last               171
_journal_paper_doi               10.1039/c5ob01690h
_journal_volume                  14
_journal_year                    2016
_chemical_formula_sum            'C18 H13 Cl N2 O'
_chemical_formula_weight         308.75
_chemical_name_systematic        3a
_space_group_IT_number           2
_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_creation_method           SHELXL-97
_audit_update_record
;
2015-04-08 deposited with the CCDC.
2015-11-05 downloaded from the CCDC.
;
_cell_angle_alpha                86.931(3)
_cell_angle_beta                 84.919(3)
_cell_angle_gamma                89.788(3)
_cell_formula_units_Z            2
_cell_length_a                   3.9823(6)
_cell_length_b                   11.7455(17)
_cell_length_c                   16.580(2)
_cell_measurement_temperature    293(2)
_cell_volume                     771.36(19)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_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  0.0232
_diffrn_reflns_av_sigmaI/netI    0.0429
_diffrn_reflns_limit_h_max       4
_diffrn_reflns_limit_h_min       -4
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            4449
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         1.74
_exptl_absorpt_coefficient_mu    0.250
_exptl_crystal_colour            Yellow
_exptl_crystal_density_diffrn    1.329
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             320
_refine_diff_density_max         0.197
_refine_diff_density_min         -0.258
_refine_diff_density_rms         0.059
_refine_ls_extinction_coef       0.016(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   1.019
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     252
_refine_ls_number_reflns         2707
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.019
_refine_ls_R_factor_all          0.0814
_refine_ls_R_factor_gt           0.0509
_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)+(0.0929P)²+0.0979P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1354
_refine_ls_wR_factor_ref         0.1617
_reflns_number_gt                1850
_reflns_number_total             2707
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c5ob01690h10.cif
_cod_data_source_block           zhaoyl140710_0m
_cod_depositor_comments          'Adding full bibliography for 7154794.cif.'
_cod_database_code               7154794
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
C1 C 1.1679(8) 0.2738(2) -0.12569(15) 0.0477(7) Uani 1 1 d
C2 C 1.1053(8) 0.1990(2) -0.18315(17) 0.0514(7) Uani 1 1 d
C3 C 0.9260(7) 0.1019(2) -0.16018(16) 0.0478(7) Uani 1 1 d
C4 C 0.8046(8) 0.0794(3) -0.08062(18) 0.0543(8) Uani 1 1 d
C5 C 0.8659(7) 0.1554(2) -0.02362(17) 0.0470(7) Uani 1 1 d
C6 C 1.0505(6) 0.2543(2) -0.04432(14) 0.0371(6) Uani 1 1 d
C7 C 1.1336(7) 0.3347(2) 0.01459(15) 0.0421(6) Uani 1 1 d
C8 C 1.0462(7) 0.3290(2) 0.09382(15) 0.0441(7) Uani 1 1 d
C9 C 1.1582(7) 0.4166(2) 0.14512(14) 0.0420(6) Uani 1 1 d
C10 C 1.0381(7) 0.4090(2) 0.23395(14) 0.0408(6) Uani 1 1 d
C11 C 1.1603(7) 0.5031(2) 0.27727(15) 0.0475(7) Uani 1 1 d
C12 C 0.7335(6) 0.2997(2) 0.34445(14) 0.0407(6) Uani 1 1 d
C13 C 0.7434(8) 0.3695(3) 0.40961(16) 0.0528(8) Uani 1 1 d
C14 C 0.6116(8) 0.3317(3) 0.48580(17) 0.0589(8) Uani 1 1 d
C15 C 0.4586(7) 0.2258(3) 0.50023(16) 0.0523(7) Uani 1 1 d
C16 C 0.4474(8) 0.1578(3) 0.43498(18) 0.0561(8) Uani 1 1 d
C17 C 0.5753(7) 0.1948(3) 0.35855(16) 0.0507(7) Uani 1 1 d
C18 C 0.3174(13) 0.1869(4) 0.5844(2) 0.0767(11) Uani 1 1 d
Cl1 Cl 0.8486(2) 0.00414(8) -0.23164(5) 0.0814(4) Uani 1 1 d
H1 H 0.634(7) 0.376(2) 0.5306(18) 0.057(8) Uiso 1 1 d
H2 H 0.841(7) 0.440(2) 0.4063(16) 0.055(8) Uiso 1 1 d
H3 H 0.561(6) 0.149(2) 0.3171(15) 0.040(7) Uiso 1 1 d
H4 H 0.316(8) 0.085(3) 0.4426(18) 0.068(9) Uiso 1 1 d
H5 H 0.909(7) 0.270(2) 0.1238(17) 0.055(8) Uiso 1 1 d
H6 H 1.266(7) 0.395(2) -0.0053(15) 0.045(7) Uiso 1 1 d
H7 H 1.300(7) 0.341(2) -0.1365(16) 0.055(8) Uiso 1 1 d
H8 H 1.175(7) 0.214(2) -0.2366(19) 0.064(9) Uiso 1 1 d
H9 H 0.689(7) 0.015(2) -0.0656(16) 0.052(8) Uiso 1 1 d
H10 H 0.781(8) 0.141(2) 0.0287(19) 0.067(9) Uiso 1 1 d
H11 H 0.141(11) 0.233(3) 0.604(3) 0.113(16) Uiso 1 1 d
H12 H 0.185(11) 0.117(4) 0.579(3) 0.117(16) Uiso 1 1 d
H13 H 0.472(13) 0.179(4) 0.620(3) 0.14(2) Uiso 1 1 d
N1 N 1.2622(8) 0.5780(2) 0.30908(16) 0.0739(8) Uani 1 1 d
N2 N 0.8567(5) 0.32432(18) 0.26341(11) 0.0410(5) Uani 1 1 d
O1 O 1.3474(6) 0.49451(17) 0.12047(11) 0.0627(6) Uani 1 1 d
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'
Cl Cl 0.1484 0.1585 '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
C2 C1 C6 121.8(3)
C2 C1 H7 124.0(16)
C6 C1 H7 114.1(16)
C3 C2 C1 119.2(3)
C3 C2 H8 119.5(18)
C1 C2 H8 121.3(19)
C2 C3 C4 120.9(2)
C2 C3 Cl1 120.2(2)
C4 C3 Cl1 118.9(2)
C5 C4 C3 119.4(3)
C5 C4 H9 119.9(17)
C3 C4 H9 120.6(17)
C4 C5 C6 121.4(3)
C4 C5 H10 118.9(19)
C6 C5 H10 119.7(19)
C5 C6 C1 117.2(2)
C5 C6 C7 123.2(2)
C1 C6 C7 119.6(2)
C8 C7 C6 127.5(2)
C8 C7 H6 116.6(16)
C6 C7 H6 115.8(16)
C7 C8 C9 120.5(2)
C7 C8 H5 126.2(16)
C9 C8 H5 113.3(16)
O1 C9 C8 123.9(2)
O1 C9 C10 117.8(2)
C8 C9 C10 118.3(2)
N2 C10 C11 127.6(2)
N2 C10 C9 119.8(2)
C11 C10 C9 112.6(2)
N1 C11 C10 177.9(3)
C17 C12 C13 117.9(2)
C17 C12 N2 114.4(2)
C13 C12 N2 127.6(2)
C14 C13 C12 120.2(3)
C14 C13 H2 115.4(17)
C12 C13 H2 124.4(17)
C13 C14 C15 121.9(3)
C13 C14 H1 120.2(17)
C15 C14 H1 117.9(17)
C16 C15 C14 117.4(2)
C16 C15 C18 122.0(3)
C14 C15 C18 120.6(3)
C17 C16 C15 121.3(3)
C17 C16 H4 119.6(17)
C15 C16 H4 118.6(17)
C16 C17 C12 121.2(3)
C16 C17 H3 119.3(15)
C12 C17 H3 119.5(15)
C15 C18 H11 112(3)
C15 C18 H12 107(3)
H11 C18 H12 98(3)
C15 C18 H13 114(3)
H11 C18 H13 111(4)
H12 C18 H13 114(4)
C10 N2 C12 128.3(2)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C1 C2 1.369(4)
C1 C6 1.395(3)
C1 H7 0.95(3)
C2 C3 1.366(4)
C2 H8 0.91(3)
C3 C4 1.376(4)
C3 Cl1 1.741(2)
C4 C5 1.373(4)
C4 H9 0.90(3)
C5 C6 1.388(3)
C5 H10 0.91(3)
C6 C7 1.453(3)
C7 C8 1.327(4)
C7 H6 0.91(3)
C8 C9 1.465(3)
C8 H5 0.97(3)
C9 O1 1.218(3)
C9 C10 1.506(3)
C10 N2 1.281(3)
C10 C11 1.457(3)
C11 N1 1.143(3)
C12 C17 1.385(4)
C12 C13 1.394(3)
C12 N2 1.404(3)
C13 C14 1.375(4)
C13 H2 0.92(3)
C14 C15 1.387(4)
C14 H1 0.94(3)
C15 C16 1.383(4)
C15 C18 1.505(4)
C16 C17 1.372(4)
C16 H4 1.00(3)
C17 H3 0.90(2)
C18 H11 0.94(4)
C18 H12 0.98(4)
C18 H13 0.89(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
C6 C1 C2 C3 -0.7(5)
C1 C2 C3 C4 0.9(5)
C1 C2 C3 Cl1 -178.9(2)
C2 C3 C4 C5 -0.2(5)
Cl1 C3 C4 C5 179.6(2)
C3 C4 C5 C6 -0.6(5)
C4 C5 C6 C1 0.7(4)
C4 C5 C6 C7 -177.3(3)
C2 C1 C6 C5 -0.1(4)
C2 C1 C6 C7 178.0(3)
C5 C6 C7 C8 -1.4(5)
C1 C6 C7 C8 -179.4(3)
C6 C7 C8 C9 178.7(2)
C7 C8 C9 O1 -4.0(4)
C7 C8 C9 C10 177.1(3)
O1 C9 C10 N2 -175.5(3)
C8 C9 C10 N2 3.4(4)
O1 C9 C10 C11 2.7(4)
C8 C9 C10 C11 -178.4(2)
N2 C10 C11 N1 172(9)
C9 C10 C11 N1 -6(9)
C17 C12 C13 C14 2.8(4)
N2 C12 C13 C14 -179.7(3)
C12 C13 C14 C15 -1.7(5)
C13 C14 C15 C16 1.0(5)
C13 C14 C15 C18 179.9(4)
C14 C15 C16 C17 -1.6(5)
C18 C15 C16 C17 179.6(3)
C15 C16 C17 C12 2.8(5)
C13 C12 C17 C16 -3.4(4)
N2 C12 C17 C16 178.8(3)
C11 C10 N2 C12 -0.9(5)
C9 C10 N2 C12 177.0(2)
C17 C12 N2 C10 -173.2(3)
C13 C12 N2 C10 9.2(5)
