#------------------------------------------------------------------------------
#$Date: 2017-10-13 10:03:29 +0200 (vie 13 de oct de 2017) $
#$Revision: 201974 $
#$URL: svn://www.crystallography.net/cod/cif/2/21/84/2218417.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided by IUCr Journals, http://journals.iucr.org/.
#
# The file may be used within the scientific community so long as
# proper attribution is given to the journal article from which the
# data were obtained.
#
data_2218417
loop_
_publ_author_name
'Oosten, Erik M. van'
'Lough, Alan J.'
'Vasdev, Neil'
_publ_section_title
;
 N-Isopropylbenzamide
;
_journal_coeditor_code           HB2729
_journal_issue                   6
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o1005
_journal_paper_doi               10.1107/S1600536808012804
_journal_volume                  64
_journal_year                    2008
_chemical_formula_iupac          'C10 H13 N O'
_chemical_formula_moiety         'C10 H13 N O'
_chemical_formula_sum            'C10 H13 N O'
_chemical_formula_weight         163.21
_chemical_name_systematic
;
N-Isopropylbenzamide
;
_space_group_IT_number           4
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                90.00
_cell_angle_beta                 104.133(7)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   5.0093(7)
_cell_length_b                   10.1250(13)
_cell_length_c                   9.6714(14)
_cell_measurement_reflns_used    2462
_cell_measurement_temperature    150.0(10)
_cell_measurement_theta_max      25.0
_cell_measurement_theta_min      3.0
_cell_volume                     475.68(11)
_computing_cell_refinement       'DENZO-SMN (Otwinowski & Minor, 1997)'
_computing_data_collection       'COLLECT (Nonius, 2002)'
_computing_data_reduction        'DENZO-SMN (Otwinowski & Minor, 1997)'
_computing_molecular_graphics    'PLATON (Spek, 2003)'
_computing_publication_material  'SHELXTL (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXTL (Sheldrick, 2008)'
_computing_structure_solution    'SIR92 (Altomare et al.,  1994)'
_diffrn_ambient_temperature      150.0(10)
_diffrn_detector_area_resol_mean 9
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Bruker Nonius KappaCCD'
_diffrn_measurement_method       'φ scans and ω scans with κ offsets'
_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  0.0613
_diffrn_reflns_av_sigmaI/netI    0.0758
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            2462
_diffrn_reflns_theta_full        25.02
_diffrn_reflns_theta_max         25.02
_diffrn_reflns_theta_min         2.96
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.074
_exptl_absorpt_correction_T_max  0.996
_exptl_absorpt_correction_T_min  0.954
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SORTAV; Blessing 1995)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.140
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             176
_exptl_crystal_size_max          0.14
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.179
_refine_diff_density_min         -0.207
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.057
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     114
_refine_ls_number_reflns         887
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.056
_refine_ls_R_factor_all          0.0953
_refine_ls_R_factor_gt           0.0573
_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)+(0.0784P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1288
_refine_ls_wR_factor_ref         0.1480
_reflns_number_gt                621
_reflns_number_total             887
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            hb2729.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21'
_cod_database_code               2218417
_cod_database_fobs_code          2218417
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z'
loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_occupancy
O O1 0.6751(6) 0.1703(3) 0.8045(3) 0.0424(8) Uani d . 1
N N1 0.2696(8) 0.1717(4) 0.8673(4) 0.0411(10) Uani d . 1
H H1N 0.103(11) 0.188(5) 0.839(5) 0.049 Uiso d . 1
C C1 0.3226(9) 0.3127(4) 0.6749(5) 0.0350(11) Uani d . 1
C C2 0.4247(10) 0.3165(5) 0.5544(5) 0.0452(13) Uani d . 1
H H2A 0.5601 0.2545 0.5432 0.054 Uiso calc R 1
C C3 0.3286(11) 0.4116(6) 0.4493(5) 0.0535(14) Uani d . 1
H H3A 0.3957 0.4126 0.3655 0.064 Uiso calc R 1
C C4 0.1377(10) 0.5034(5) 0.4666(6) 0.0516(14) Uani d . 1
H H4A 0.0734 0.5682 0.3951 0.062 Uiso calc R 1
C C5 0.0391(11) 0.5014(5) 0.5883(6) 0.0523(14) Uani d . 1
H H5A -0.0912 0.5656 0.6010 0.063 Uiso calc R 1
C C6 0.1296(9) 0.4064(5) 0.6915(5) 0.0451(13) Uani d . 1
H H6A 0.0597 0.4051 0.7744 0.054 Uiso calc R 1
C C7 0.4356(8) 0.2117(4) 0.7864(4) 0.0362(12) Uani d . 1
C C8 0.3461(10) 0.0743(5) 0.9808(5) 0.0474(13) Uani d . 1
H H8A 0.5489 0.0586 0.9996 0.057 Uiso calc R 1
C C9 0.1984(13) -0.0561(5) 0.9351(6) 0.0648(16) Uani d . 1
H H9A 0.2525 -0.0903 0.8512 0.097 Uiso calc R 1
H H9B -0.0011 -0.0417 0.9116 0.097 Uiso calc R 1
H H9C 0.2488 -0.1200 1.0132 0.097 Uiso calc R 1
C C10 0.2833(11) 0.1271(6) 1.1160(5) 0.0556(15) Uani d . 1
H H10A 0.3743 0.2126 1.1400 0.083 Uiso calc R 1
H H10B 0.3510 0.0647 1.1942 0.083 Uiso calc R 1
H H10C 0.0839 0.1380 1.1013 0.083 Uiso calc R 1
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_12
_atom_site_aniso_U_13
_atom_site_aniso_U_23
O1 0.0319(17) 0.0442(18) 0.0515(17) 0.0024(15) 0.0112(13) 0.0032(16)
N1 0.0326(19) 0.046(2) 0.047(2) 0.003(2) 0.0149(18) 0.012(2)
C1 0.033(2) 0.035(2) 0.039(3) -0.006(2) 0.012(2) 0.000(2)
C2 0.049(3) 0.044(3) 0.046(3) 0.001(2) 0.019(2) 0.003(2)
C3 0.057(3) 0.061(3) 0.046(3) -0.003(3) 0.019(3) 0.012(3)
C4 0.049(3) 0.051(3) 0.050(3) -0.002(3) 0.004(3) 0.020(3)
C5 0.053(3) 0.040(3) 0.066(3) 0.007(3) 0.017(3) 0.013(3)
C6 0.046(3) 0.042(3) 0.051(3) 0.003(2) 0.017(2) 0.005(3)
C7 0.035(3) 0.034(3) 0.037(2) -0.004(2) 0.005(2) -0.008(2)
C8 0.041(3) 0.054(3) 0.048(3) 0.012(3) 0.012(2) 0.017(3)
C9 0.085(4) 0.043(3) 0.064(3) 0.010(3) 0.014(3) 0.012(3)
C10 0.062(3) 0.062(4) 0.044(3) -0.001(3) 0.015(2) 0.012(3)
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
C7 N1 C8 124.0(4)
C7 N1 H1N 118(4)
C8 N1 H1N 117(4)
C2 C1 C6 119.2(4)
C2 C1 C7 118.3(4)
C6 C1 C7 122.4(4)
C1 C2 C3 120.0(5)
C1 C2 H2A 120.0
C3 C2 H2A 120.0
C4 C3 C2 120.3(5)
C4 C3 H3A 119.9
C2 C3 H3A 119.9
C3 C4 C5 119.8(5)
C3 C4 H4A 120.1
C5 C4 H4A 120.1
C6 C5 C4 120.2(5)
C6 C5 H5A 119.9
C4 C5 H5A 119.9
C5 C6 C1 120.5(4)
C5 C6 H6A 119.8
C1 C6 H6A 119.8
O1 C7 N1 122.2(4)
O1 C7 C1 121.0(4)
N1 C7 C1 116.7(4)
N1 C8 C10 109.9(4)
N1 C8 C9 110.4(4)
C10 C8 C9 111.5(4)
N1 C8 H8A 108.3
C10 C8 H8A 108.3
C9 C8 H8A 108.3
C8 C9 H9A 109.5
C8 C9 H9B 109.5
H9A C9 H9B 109.5
C8 C9 H9C 109.5
H9A C9 H9C 109.5
H9B C9 H9C 109.5
C8 C10 H10A 109.5
C8 C10 H10B 109.5
H10A C10 H10B 109.5
C8 C10 H10C 109.5
H10A C10 H10C 109.5
H10B C10 H10C 109.5
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O1 C7 1.242(5)
N1 C7 1.337(6)
N1 C8 1.455(6)
N1 H1N 0.83(5)
C1 C2 1.383(6)
C1 C6 1.392(6)
C1 C7 1.493(6)
C2 C3 1.398(8)
C2 H2A 0.9500
C3 C4 1.373(7)
C3 H3A 0.9500
C4 C5 1.384(7)
C4 H4A 0.9500
C5 C6 1.380(7)
C5 H5A 0.9500
C6 H6A 0.9500
C8 C10 1.516(7)
C8 C9 1.525(8)
C8 H8A 1.0000
C9 H9A 0.9800
C9 H9B 0.9800
C9 H9C 0.9800
C10 H10A 0.9800
C10 H10B 0.9800
C10 H10C 0.9800
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
N1 H1N O1 1_455 0.83(5) 2.10(5) 2.890(5) 160(5)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 71813
