#------------------------------------------------------------------------------
#$Date: 2017-10-14 22:27:35 +0300 (Sat, 14 Oct 2017) $
#$Revision: 202017 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/20/41/7204197.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_7204197
loop_
_publ_author_name
'Karlsen, Hege'
'Kolsaker, Per'
'Rømming, Christian'
'Uggerud, Einar'
_publ_section_title
;
 The analogy between CO and C(CN)2. Part 2.1 Structural
 properties of N,N-dialkylaminobenzamides and the analogously
 substituted 2-(phenylmethylene)propanedinitriles
;
_journal_issue                   3
_journal_name_full
'Journal of the Chemical Society, Perkin Transactions 2'
_journal_page_first              404
_journal_paper_doi               10.1039/b105532c
_journal_year                    2002
_chemical_formula_sum            'C9 H11 N O'
_chemical_formula_weight         149.19
_chemical_name_systematic
; 
N,N-dimetyl-benzamide 
;
_space_group_IT_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_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   6.6312(5)
_cell_length_b                   7.6519(6)
_cell_length_c                   16.3025(13)
_cell_measurement_temperature    293(2)
_cell_volume                     827.21(11)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.952
_diffrn_measured_fraction_theta_max 0.952
_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  0.0301
_diffrn_reflns_av_sigmaI/netI    0.0214
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_number            16518
_diffrn_reflns_theta_full        40.01
_diffrn_reflns_theta_max         40.01
_diffrn_reflns_theta_min         8.23
_exptl_absorpt_coefficient_mu    0.079
_exptl_absorpt_correction_type   SADABS
_exptl_crystal_density_diffrn    1.198
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             320
_exptl_crystal_size_max          0.8
_exptl_crystal_size_mid          0.6
_exptl_crystal_size_min          0.2
_refine_diff_density_max         0.493
_refine_diff_density_min         -0.271
_refine_diff_density_rms         0.052
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.7(8)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.138
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     144
_refine_ls_number_reflns         4831
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.138
_refine_ls_R_factor_all          0.0462
_refine_ls_R_factor_gt           0.0399
_refine_ls_shift/su_max          0.012
_refine_ls_shift/su_mean         0.002
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w==1/[σ²(Fo²)+(0.0630P)²+0.0400P] where P==(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1030
_refine_ls_wR_factor_ref         0.1092
_reflns_number_gt                4433
_reflns_number_total             4831
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            b105532c.txt
_cod_data_source_block           5a
_cod_original_sg_symbol_H-M      P2(1)2(1)2(1)
_cod_database_code               7204197
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 1.21437(9) 0.15748(9) 0.19790(4) 0.02870(12) Uani 1 1 d . . .
N1 N 0.87964(9) 0.09714(8) 0.19412(4) 0.02167(10) Uani 1 1 d . . .
C4 C 1.06446(9) 0.10522(8) 0.15942(4) 0.01865(9) Uani 1 1 d . . .
C5 C 1.08769(8) 0.05291(8) 0.07098(3) 0.01691(9) Uani 1 1 d . . .
C6 C 0.96819(10) 0.12545(9) 0.00893(4) 0.02128(11) Uani 1 1 d . . .
H6 H 0.860(2) 0.2071(18) 0.0217(9) 0.030(3) Uiso 1 1 d . . .
C7 C 1.00550(12) 0.08411(10) -0.07323(4) 0.02473(12) Uani 1 1 d . . .
H7 H 0.918(2) 0.139(2) -0.1152(10) 0.038(4) Uiso 1 1 d . . .
C8 C 1.16106(13) -0.02991(10) -0.09391(4) 0.02643(13) Uani 1 1 d . . .
H8 H 1.189(2) -0.057(2) -0.1485(10) 0.035(4) Uiso 1 1 d . . .
C9 C 1.28085(11) -0.10212(10) -0.03215(4) 0.02446(12) Uani 1 1 d . . .
H9 H 1.398(3) -0.182(3) -0.0432(11) 0.049(4) Uiso 1 1 d . . .
C10 C 1.24557(9) -0.05994(9) 0.04984(4) 0.01975(10) Uani 1 1 d . . .
H10 H 1.335(2) -0.112(2) 0.0931(9) 0.033(3) Uiso 1 1 d . . .
C11 C 0.85541(15) 0.15927(14) 0.27798(5) 0.03453(18) Uani 1 1 d . . .
H11A H 0.852(3) 0.064(3) 0.3134(13) 0.056(5) Uiso 1 1 d . . .
H11B H 0.715(4) 0.211(3) 0.2836(16) 0.069(6) Uiso 1 1 d . . .
H11C H 0.971(3) 0.239(3) 0.2895(12) 0.053(5) Uiso 1 1 d . . .
C12 C 0.70667(11) 0.00246(10) 0.16159(5) 0.02501(12) Uani 1 1 d . . .
H12A H 0.677(3) -0.098(2) 0.2002(11) 0.042(4) Uiso 1 1 d . . .
H12B H 0.733(3) -0.038(2) 0.1100(11) 0.037(4) Uiso 1 1 d . . .
H12C H 0.586(3) 0.075(2) 0.1600(10) 0.039(4) Uiso 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'
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
_geom_angle_publ_flag
C4 N1 C11 118.56(6) . . ?
C4 N1 C12 125.78(6) . . ?
C11 N1 C12 114.66(6) . . ?
O1 C4 N1 121.97(6) . . ?
O1 C4 C5 119.21(5) . . ?
N1 C4 C5 118.81(5) . . ?
C6 C5 C10 119.35(5) . . ?
C6 C5 C4 121.95(5) . . ?
C10 C5 C4 118.46(5) . . ?
C7 C6 C5 120.15(6) . . ?
C7 C6 H6 118.7(8) . . ?
C5 C6 H6 121.2(8) . . ?
C8 C7 C6 120.31(6) . . ?
C8 C7 H7 122.2(9) . . ?
C6 C7 H7 117.5(9) . . ?
C7 C8 C9 119.65(6) . . ?
C7 C8 H8 121.2(10) . . ?
C9 C8 H8 119.1(10) . . ?
C10 C9 C8 120.26(6) . . ?
C10 C9 H9 116.3(10) . . ?
C8 C9 H9 123.4(10) . . ?
C9 C10 C5 120.26(6) . . ?
C9 C10 H10 118.8(9) . . ?
C5 C10 H10 120.9(9) . . ?
N1 C11 H11A 109.1(13) . . ?
N1 C11 H11B 108.3(14) . . ?
H11A C11 H11B 103(2) . . ?
N1 C11 H11C 106.9(12) . . ?
H11A C11 H11C 112.4(17) . . ?
H11B C11 H11C 116.5(17) . . ?
N1 C12 H12A 107.7(10) . . ?
N1 C12 H12B 110.7(11) . . ?
H12A C12 H12B 110.5(15) . . ?
N1 C12 H12C 112.0(10) . . ?
H12A C12 H12C 106.8(15) . . ?
H12B C12 H12C 109.0(15) . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C4 1.2416(8) . ?
N1 C4 1.3512(8) . ?
N1 C11 1.4564(10) . ?
N1 C12 1.4565(9) . ?
C4 C5 1.5044(8) . ?
C5 C6 1.3997(9) . ?
C5 C10 1.4001(9) . ?
C6 C7 1.3983(10) . ?
C6 H6 0.973(14) . ?
C7 C8 1.3925(11) . ?
C7 H7 0.992(16) . ?
C8 C9 1.3964(11) . ?
C8 H8 0.932(17) . ?
C9 C10 1.3949(9) . ?
C9 H9 1.00(2) . ?
C10 H10 1.005(15) . ?
C11 H11A 0.93(2) . ?
C11 H11B 1.01(2) . ?
C11 H11C 1.00(2) . ?
C12 H12A 1.016(17) . ?
C12 H12B 0.913(17) . ?
C12 H12C 0.974(17) . ?
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
_geom_torsion_publ_flag
C11 N1 C4 O1 2.81(11) . . . . ?
C12 N1 C4 O1 -165.08(7) . . . . ?
C11 N1 C4 C5 -175.83(7) . . . . ?
C12 N1 C4 C5 16.28(10) . . . . ?
O1 C4 C5 C6 -125.73(8) . . . . ?
N1 C4 C5 C6 52.96(9) . . . . ?
O1 C4 C5 C10 48.52(9) . . . . ?
N1 C4 C5 C10 -132.79(7) . . . . ?
C10 C5 C6 C7 0.55(10) . . . . ?
C4 C5 C6 C7 174.75(6) . . . . ?
C5 C6 C7 C8 0.26(11) . . . . ?
C6 C7 C8 C9 -0.42(12) . . . . ?
C7 C8 C9 C10 -0.23(12) . . . . ?
C8 C9 C10 C5 1.04(11) . . . . ?
C6 C5 C10 C9 -1.20(9) . . . . ?
C4 C5 C10 C9 -175.60(6) . . . . ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 11422
