#------------------------------------------------------------------------------
#$Date: 2017-10-13 09:09:21 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201973 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/20/87/2208773.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_2208773
loop_
_publ_author_name
'Warzecha, Klaus-Dieter'
'Lex, Johann'
'Neudörfl, Jörg M.'
'Griesbeck, Axel G.'
_publ_section_title
;
 N-(2-Phenethyl)phthalimide
;
_journal_issue                   4
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o1580
_journal_page_last               o1581
_journal_paper_doi               10.1107/S1600536806010154
_journal_volume                  62
_journal_year                    2006
_chemical_formula_iupac          'C16 H13 N O2'
_chemical_formula_moiety         'C16 H13 N O2'
_chemical_formula_sum            'C16 H13 N O2'
_chemical_formula_weight         251.27
_chemical_melting_point          401
_chemical_name_common
;
 N-(2-phenethyl)phthalimide
;
_chemical_name_systematic
;
 2-phenethylisoindoline-1,3-dione
;
_space_group_IT_number           61
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  '-P 2ac 2ab'
_symmetry_space_group_name_H-M   'P b c a'
_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            8
_cell_length_a                   28.3243(9)
_cell_length_b                   11.4545(3)
_cell_length_c                   7.6680(2)
_cell_measurement_reflns_used    10877
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      27.0
_cell_measurement_theta_min      2.3
_cell_volume                     2487.81(12)
_computing_cell_refinement       'DENZO (Otwinowski & Minor, 1997)'
_computing_data_collection       'COLLECT (Hooft, 1999)'
_computing_data_reduction        DENZO
_computing_molecular_graphics    'SCHAKAL99 (Keller, 1999)'
_computing_publication_material
;
SHELXL97,
PLATON (Spek, 2003) and
enCIFer (Allen et al.,  2004)
;
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_device_type  'Nonius KappaCCD'
_diffrn_measurement_method       'φ/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  0.067
_diffrn_reflns_av_sigmaI/netI    0.066
_diffrn_reflns_limit_h_max       27
_diffrn_reflns_limit_h_min       -36
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            10877
_diffrn_reflns_theta_full        27.0
_diffrn_reflns_theta_max         27.0
_diffrn_reflns_theta_min         2.3
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.09
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.342
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       'cube cut from a thick platelet'
_exptl_crystal_F_000             1056
_exptl_crystal_size_max          0.42
_exptl_crystal_size_mid          0.40
_exptl_crystal_size_min          0.40
_refine_diff_density_max         0.21
_refine_diff_density_min         -0.24
_refine_ls_extinction_coef       0.0058(8)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL97
_refine_ls_goodness_of_fit_ref   0.99
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     225
_refine_ls_number_reflns         2700
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.99
_refine_ls_R_factor_all          0.081
_refine_ls_R_factor_gt           0.041
_refine_ls_shift/su_max          0.019
_refine_ls_shift/su_mean         0.002
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0441P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.083
_refine_ls_wR_factor_ref         0.095
_reflns_number_gt                1790
_reflns_number_total             2700
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            ya2002.cif
_cod_data_source_block           I
_cod_database_code               2208773
_cod_database_fobs_code          2208773
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'x+1/2, -y+1/2, -z'
'-x, y+1/2, -z+1/2'
'-x+1/2, -y, z+1/2'
'-x, -y, -z'
'-x-1/2, y-1/2, z'
'x, -y-1/2, z-1/2'
'x-1/2, y, -z-1/2'
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_occupancy
C C1 0.56767(5) 0.99021(13) -0.22494(18) 0.0199(4) Uani d 1
C C2 0.56150(5) 0.82365(13) -0.05709(19) 0.0212(4) Uani d 1
C C3 0.51349(5) 0.85514(13) -0.11879(18) 0.0189(3) Uani d 1
C C4 0.47047(6) 0.80330(14) -0.0875(2) 0.0236(4) Uani d 1
C C5 0.43074(6) 0.85466(14) -0.1621(2) 0.0257(4) Uani d 1
C C6 0.43457(6) 0.95494(14) -0.2624(2) 0.0248(4) Uani d 1
C C7 0.47807(5) 1.00758(14) -0.29280(19) 0.0217(4) Uani d 1
C C8 0.51736(5) 0.95540(12) -0.22009(17) 0.0183(3) Uani d 1
C C9 0.64172(5) 0.91659(15) -0.08252(19) 0.0226(4) Uani d 1
C C10 0.67270(5) 0.86116(16) -0.2219(2) 0.0249(4) Uani d 1
C C11 0.72388(5) 0.86486(13) -0.16927(18) 0.0203(4) Uani d 1
C C12 0.75271(5) 0.95909(13) -0.21241(18) 0.0215(4) Uani d 1
C C13 0.79932(5) 0.96204(14) -0.1583(2) 0.0236(4) Uani d 1
C C14 0.81823(6) 0.87171(14) -0.05967(19) 0.0234(4) Uani d 1
C C15 0.78974(6) 0.77761(14) -0.01613(19) 0.0239(4) Uani d 1
C C16 0.74308(6) 0.77484(13) -0.07092(19) 0.0225(4) Uani d 1
N N1 0.59159(4) 0.90951(10) -0.12183(14) 0.0192(3) Uani d 1
O O1 0.58628(4) 1.07163(9) -0.29930(13) 0.0274(3) Uani d 1
O O2 0.57394(4) 0.74178(9) 0.03240(14) 0.0303(3) Uani d 1
H H4 0.4670(6) 0.7341(13) -0.018(2) 0.031(5) Uiso d 1
H H5 0.3993(6) 0.8181(14) -0.1393(19) 0.036(5) Uiso d 1
H H6 0.4068(6) 0.9888(13) -0.3110(19) 0.031(5) Uiso d 1
H H7 0.4802(5) 1.0784(13) -0.3649(19) 0.026(4) Uiso d 1
H H9A 0.6493(6) 1.0029(14) -0.0714(19) 0.036(5) Uiso d 1
H H9B 0.6459(5) 0.8762(14) 0.030(2) 0.033(4) Uiso d 1
H H10A 0.6681(5) 0.9039(13) -0.332(2) 0.035(5) Uiso d 1
H H10B 0.6617(6) 0.7778(15) -0.2343(19) 0.036(5) Uiso d 1
H H12 0.7401(5) 1.0236(12) -0.2832(19) 0.026(4) Uiso d 1
H H13 0.8202(6) 1.0323(13) -0.1907(18) 0.029(4) Uiso d 1
H H14 0.8512(6) 0.8719(13) -0.0199(18) 0.032(4) Uiso d 1
H H15 0.8022(5) 0.7113(14) 0.057(2) 0.036(5) Uiso d 1
H H16 0.7236(6) 0.7060(14) -0.042(2) 0.034(5) Uiso d 1
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
O1 C1 N1 124.45(14)
O1 C1 C8 129.56(14)
N1 C1 C8 105.99(12)
O2 C2 N1 124.70(14)
O2 C2 C3 129.31(14)
N1 C2 C3 105.98(12)
C4 C3 C8 121.54(14)
C4 C3 C2 130.59(14)
C8 C3 C2 107.85(12)
C3 C4 C5 117.48(15)
C3 C4 H4 122.8(10)
C5 C4 H4 119.7(10)
C6 C5 C4 120.97(15)
C6 C5 H5 120.9(9)
C4 C5 H5 118.1(9)
C5 C6 C7 121.41(15)
C5 C6 H6 119.3(10)
C7 C6 H6 119.2(10)
C8 C7 C6 117.28(15)
C8 C7 H7 122.3(9)
C6 C7 H7 120.4(9)
C7 C8 C3 121.30(14)
C7 C8 C1 130.48(14)
C3 C8 C1 108.19(13)
N1 C9 C10 113.22(12)
N1 C9 H9A 106.1(9)
C10 C9 H9A 110.1(9)
N1 C9 H9B 105.9(9)
C10 C9 H9B 110.4(9)
H9A C9 H9B 111.0(13)
C11 C10 C9 110.80(12)
C11 C10 H10A 110.1(9)
C9 C10 H10A 108.5(9)
C11 C10 H10B 110.4(9)
C9 C10 H10B 106.5(9)
H10A C10 H10B 110.5(13)
C16 C11 C12 118.34(14)
C16 C11 C10 120.13(14)
C12 C11 C10 121.50(14)
C13 C12 C11 120.45(15)
C13 C12 H12 119.6(9)
C11 C12 H12 119.9(9)
C12 C13 C14 120.85(15)
C12 C13 H13 119.7(9)
C14 C13 H13 119.4(9)
C13 C14 C15 119.04(15)
C13 C14 H14 122.3(9)
C15 C14 H14 118.7(9)
C16 C15 C14 119.94(15)
C16 C15 H15 118.9(9)
C14 C15 H15 121.1(9)
C15 C16 C11 121.38(15)
C15 C16 H16 118.7(9)
C11 C16 H16 119.9(9)
C1 N1 C2 111.93(12)
C1 N1 C9 123.78(12)
C2 N1 C9 124.27(13)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C1 O1 1.2137(16)
C1 N1 1.3924(18)
C1 C8 1.480(2)
C2 O2 1.2143(17)
C2 N1 1.3928(18)
C2 C3 1.484(2)
C3 C4 1.377(2)
C3 C8 1.391(2)
C4 C5 1.393(2)
C4 H4 0.962(15)
C5 C6 1.386(2)
C5 H5 0.999(16)
C6 C7 1.391(2)
C6 H6 0.952(16)
C7 C8 1.381(2)
C7 H7 0.984(15)
C9 N1 1.4536(18)
C9 C10 1.522(2)
C9 H9A 1.015(15)
C9 H9B 0.986(15)
C10 C11 1.505(2)
C10 H10A 0.984(15)
C10 H10B 1.008(17)
C11 C16 1.389(2)
C11 C12 1.393(2)
C12 C13 1.384(2)
C12 H12 0.984(15)
C13 C14 1.389(2)
C13 H13 1.030(16)
C14 C15 1.387(2)
C14 H14 0.982(16)
C15 C16 1.387(2)
C15 H15 1.009(17)
C16 H16 0.988(16)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 309454
