#------------------------------------------------------------------------------
#$Date: 2016-03-21 05:34:46 +0200 (Mon, 21 Mar 2016) $
#$Revision: 178485 $
#$URL: svn://www.crystallography.net/cod/cif/4/03/06/4030669.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_4030669
loop_
_publ_author_name
'Wagner, Alexander'
'Ofial, Armin R.'
_publ_section_title
;
 Potassium Thiocyanate as Source of Cyanide for the Oxidative α-Cyanation
 of Tertiary Amines.
;
_journal_issue                   5
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              2848
_journal_page_last               2854
_journal_paper_doi               10.1021/jo502846c
_journal_volume                  80
_journal_year                    2015
_chemical_absolute_configuration unk
_chemical_formula_moiety         'C9 H12 N2 O'
_chemical_formula_sum            'C9 H12 N2 O'
_chemical_formula_weight         164.204
_space_group_IT_number           19
_symmetry_cell_setting           orthorhombic
_symmetry_Int_Tables_number      19
_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_block_code                C9H12N2O_sv065_mayr
_audit_creation_method           'form98_non/compatible with shelxl97-2'
_audit_update_record             17-Apr-14
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   6.6807(5)
_cell_length_b                   7.3529(6)
_cell_length_c                   17.0246(13)
_cell_measurement_reflns_used    7869
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      26.2508
_cell_measurement_theta_min      3.0177
_cell_volume                     836.29(11)
_computing_cell_refinement       'APEX2 v2012.4-3 (Bruker AXS)'
_computing_data_collection       'Bruker Instrument Service v3.0.21'
_computing_data_reduction        'SAINT V8.18C (Bruker AXS Inc., 2011)'
_computing_structure_refinement
;
Sheldrick, G. M. (2008).
Acta Cryst. A64, 112--122.
;
_computing_structure_solution
;
A. Altomare, M. C. Burla, M. Camalli, G. L. Cascarano, C. Giacovazzo, A.
Guagliardi, A. G. G. Moliterni, G. Polidori, R. Spagna: SIR97: a new tool for
crystal structure determination and refinement; J. Appl. Crystallogr. 1999,
32, 115-119.
;
_diffrn_ambient_temperature      173(2)
_diffrn_detector_area_resol_mean 10.4167
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device       'fixed-chi three-circle diffractometer'
_diffrn_measurement_device_type  'Bruker D8Venture'
_diffrn_measurement_method       'mix of phi and omega scans'
_diffrn_radiation_collimation    0.8_mm
_diffrn_radiation_monochromator  'focusing mirrors'
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0383
_diffrn_reflns_av_sigmaI/netI    0.0157
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            21210
_diffrn_reflns_theta_full        26.43
_diffrn_reflns_theta_max         26.36
_diffrn_reflns_theta_min         3.02
_diffrn_source_current           50
_diffrn_source_power             2.5
_diffrn_source_type              'Bruker TXS'
_diffrn_source_voltage           50
_exptl_absorpt_coefficient_mu    0.087
_exptl_absorpt_correction_T_max  0.9585
_exptl_absorpt_correction_T_min  0.9291
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS V2012/1 (Bruker AXS Inc.)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.30420(17)
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             352
_exptl_crystal_size_max          0.130
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.060
_refine_diff_density_max         0.149
_refine_diff_density_min         -0.152
_refine_diff_density_rms         0.034
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   1.4(16)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.090
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     109
_refine_ls_number_reflns         1723
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.090
_refine_ls_R_factor_all          0.0353
_refine_ls_R_factor_gt           0.0310
_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)+(0.0336P)²+0.1928P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0740
_refine_ls_wR_factor_ref         0.0761
_reflns_number_gt                1608
_reflns_number_total             1723
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo502846c_si_002.cif
_cod_data_source_block           sv065
_cod_depositor_comments          'Adding full bibliography for 4030669.cif.'
_cod_database_code               4030669
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'x+1/2, -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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
C1 C 0.1518(2) -0.08763(19) 0.40884(8) 0.0285(3) Uani 1 1 d .
H1A H 0.2594 -0.1338 0.3742 0.034 Uiso 1 1 calc R
H1B H 0.0222 -0.1334 0.3887 0.034 Uiso 1 1 calc R
C2 C 0.1837(2) -0.15351(19) 0.48926(9) 0.0280(3) Uani 1 1 d .
C3 C 0.1025(2) 0.1951(2) 0.33235(8) 0.0255(3) Uani 1 1 d .
H3 H -0.0376 0.1645 0.3164 0.031 Uiso 1 1 calc R
C4 C 0.2515(2) 0.1424(2) 0.26732(8) 0.0275(3) Uani 1 1 d .
H4A H 0.2333 0.0123 0.2541 0.033 Uiso 1 1 calc R
H4B H 0.2220 0.2145 0.2196 0.033 Uiso 1 1 calc R
C5 C 0.4655(2) 0.17390(19) 0.29095(8) 0.0244(3) Uani 1 1 d .
C6 C 0.5148(2) 0.1419(2) 0.37613(8) 0.0287(3) Uani 1 1 d .
H6A H 0.6364 0.2116 0.3902 0.034 Uiso 1 1 calc R
H6B H 0.5434 0.0112 0.3845 0.034 Uiso 1 1 calc R
C7 C 0.3406(2) 0.20032(18) 0.42973(7) 0.0231(3) Uani 1 1 d .
H7 H 0.3737 0.1774 0.4861 0.028 Uiso 1 1 calc R
C8 C 0.2862(2) 0.4002(2) 0.41658(9) 0.0325(3) Uani 1 1 d .
H8A H 0.4036 0.4698 0.3978 0.039 Uiso 1 1 calc R
H8B H 0.2366 0.4562 0.4657 0.039 Uiso 1 1 calc R
C9 C 0.1201(2) 0.3959(2) 0.35358(9) 0.0326(3) Uani 1 1 d .
H9A H -0.0077 0.4428 0.3749 0.039 Uiso 1 1 calc R
H9B H 0.1583 0.4692 0.3072 0.039 Uiso 1 1 calc R
N1 N 0.15191(16) 0.11076(15) 0.40816(6) 0.0216(2) Uani 1 1 d .
N2 N 0.2101(2) -0.20474(19) 0.55139(8) 0.0385(3) Uani 1 1 d .
O1 O 0.59217(17) 0.22116(16) 0.24423(7) 0.0392(3) Uani 1 1 d .
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
C1 0.0361(8) 0.0248(7) 0.0247(7) -0.0018(6) 0.0069(6) -0.0075(6)
C2 0.0307(7) 0.0205(7) 0.0329(7) -0.0004(6) 0.0101(6) 0.0017(6)
C3 0.0181(7) 0.0355(8) 0.0229(6) 0.0037(6) -0.0016(5) -0.0012(6)
C4 0.0292(7) 0.0358(8) 0.0175(6) 0.0020(6) -0.0015(5) -0.0006(6)
C5 0.0257(7) 0.0229(7) 0.0245(6) 0.0004(5) 0.0056(6) 0.0022(5)
C6 0.0195(6) 0.0367(8) 0.0297(7) 0.0054(6) -0.0028(6) -0.0005(6)
C7 0.0255(6) 0.0251(7) 0.0186(6) 0.0000(5) -0.0021(5) -0.0044(6)
C8 0.0434(9) 0.0229(7) 0.0311(8) -0.0022(6) 0.0040(6) -0.0057(6)
C9 0.0344(8) 0.0305(8) 0.0329(8) 0.0070(6) 0.0065(6) 0.0089(7)
N1 0.0223(5) 0.0230(6) 0.0195(5) -0.0003(5) 0.0027(5) -0.0022(5)
N2 0.0446(8) 0.0342(7) 0.0369(8) 0.0068(6) 0.0067(6) 0.0081(6)
O1 0.0343(6) 0.0484(7) 0.0349(6) 0.0038(5) 0.0143(5) -0.0046(5)
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
N1 C1 C2 109.72(11)
N1 C1 H1A 109.7
C2 C1 H1A 109.7
N1 C1 H1B 109.7
C2 C1 H1B 109.7
H1A C1 H1B 108.2
N2 C2 C1 179.38(17)
N1 C3 C9 100.54(10)
N1 C3 C4 112.36(11)
C9 C3 C4 111.38(12)
N1 C3 H3 110.7
C9 C3 H3 110.7
C4 C3 H3 110.7
C5 C4 C3 112.58(11)
C5 C4 H4A 109.1
C3 C4 H4A 109.1
C5 C4 H4B 109.1
C3 C4 H4B 109.1
H4A C4 H4B 107.8
O1 C5 C4 122.18(13)
O1 C5 C6 121.59(13)
C4 C5 C6 116.23(11)
C5 C6 C7 111.20(11)
C5 C6 H6A 109.4
C7 C6 H6A 109.4
C5 C6 H6B 109.4
C7 C6 H6B 109.4
H6A C6 H6B 108.0
N1 C7 C8 100.96(11)
N1 C7 C6 112.04(11)
C8 C7 C6 111.15(11)
N1 C7 H7 110.8
C8 C7 H7 110.8
C6 C7 H7 110.8
C7 C8 C9 104.64(11)
C7 C8 H8A 110.8
C9 C8 H8A 110.8
C7 C8 H8B 110.8
C9 C8 H8B 110.8
H8A C8 H8B 108.9
C3 C9 C8 103.89(12)
C3 C9 H9A 111.0
C8 C9 H9A 111.0
C3 C9 H9B 111.0
C8 C9 H9B 111.0
H9A C9 H9B 109.0
C1 N1 C7 116.54(11)
C1 N1 C3 115.39(11)
C7 N1 C3 102.90(10)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C1 N1 1.4588(17)
C1 C2 1.468(2)
C1 H1A 0.9900
C1 H1B 0.9900
C2 N2 1.1367(19)
C3 N1 1.4693(16)
C3 C9 1.525(2)
C3 C4 1.5385(19)
C3 H3 1.0000
C4 C5 1.5027(19)
C4 H4A 0.9900
C4 H4B 0.9900
C5 O1 1.2125(16)
C5 C6 1.5056(19)
C6 C7 1.5400(19)
C6 H6A 0.9900
C6 H6B 0.9900
C7 N1 1.4688(17)
C7 C8 1.530(2)
C7 H7 1.0000
C8 C9 1.543(2)
C8 H8A 0.9900
C8 H8B 0.9900
C9 H9A 0.9900
C9 H9B 0.9900
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
N1 C3 C4 C5 -51.64(16)
C9 C3 C4 C5 60.29(16)
C3 C4 C5 O1 -145.92(14)
C3 C4 C5 C6 34.61(18)
O1 C5 C6 C7 144.55(14)
C4 C5 C6 C7 -35.97(17)
C5 C6 C7 N1 55.12(15)
C5 C6 C7 C8 -57.00(15)
N1 C7 C8 C9 -26.80(13)
C6 C7 C8 C9 92.19(13)
N1 C3 C9 C8 32.25(13)
C4 C3 C9 C8 -86.99(13)
C7 C8 C9 C3 -3.36(14)
C2 C1 N1 C7 64.66(15)
C2 C1 N1 C3 -174.46(12)
C8 C7 N1 C1 176.18(11)
C6 C7 N1 C1 57.82(15)
C8 C7 N1 C3 48.88(12)
C6 C7 N1 C3 -69.48(13)
C9 C3 N1 C1 -179.22(11)
C4 C3 N1 C1 -60.70(15)
C9 C3 N1 C7 -51.20(12)
C4 C3 N1 C7 67.32(13)
