#------------------------------------------------------------------------------
#$Date: 2017-10-13 11:03:29 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201974 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/21/09/2210973.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_2210973
loop_
_publ_author_name
'Warzecha, Klaus-Dieter'
'Lex, Johann'
'Griesbeck, Axel G.'
_publ_section_title
;
 N-(2-Methoxybenzyl)phthalimide: a two-dimensional network of
 C(7) and C(9) chain motifs
;
_journal_coeditor_code           DN2082
_journal_issue                   11
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o5271
_journal_page_last               o5273
_journal_paper_doi               10.1107/S1600536806044060
_journal_volume                  62
_journal_year                    2006
_chemical_formula_moiety         'C16 H13 N O3'
_chemical_formula_sum            'C16 H13 N O3'
_chemical_formula_weight         267.27
_chemical_melting_point          412
_chemical_name_common
;
N-(2-Methoxybenzyl)phthalimide
;
_chemical_name_systematic
;
2-(2-methoxybenzyl)isoindoline-1,3-dione
;
_space_group_IT_number           29
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2c -2ac'
_symmetry_space_group_name_H-M   'P c a 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL97
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   16.2809(14)
_cell_length_b                   10.4277(7)
_cell_length_c                   7.5585(5)
_cell_measurement_reflns_used    5269
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      27.00
_cell_measurement_theta_min      1.95
_cell_volume                     1283.22(16)
_computing_cell_refinement       'DENZO (Otwinowski & Minor, 1997)'
_computing_data_collection       'COLLECT (Nonius, 1999)'
_computing_data_reduction        DENZO
_computing_molecular_graphics    'SCHAKAL99 (Keller & Pierrard, 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 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Nonius KappaCCD area-detector'
_diffrn_measurement_method       'φ and ω'
_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  0.0457
_diffrn_reflns_av_sigmaI/netI    0.0549
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -6
_diffrn_reflns_number            5269
_diffrn_reflns_theta_full        27.00
_diffrn_reflns_theta_max         27.00
_diffrn_reflns_theta_min         1.95
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.096
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.383
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             560
_exptl_crystal_size_max          0.44
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.22
_refine_diff_density_max         0.154
_refine_diff_density_min         -0.180
_refine_ls_extinction_coef       0.0079(17)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL97 (Sheldrick, 1997)'
_refine_ls_goodness_of_fit_ref   1.008
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     230
_refine_ls_number_reflns         1514
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.008
_refine_ls_R_factor_all          0.0553
_refine_ls_R_factor_gt           0.0353
_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)+(0.0313P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0616
_refine_ls_wR_factor_ref         0.0663
_reflns_number_gt                1204
_reflns_number_total             1514
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            dn2082.cif
_cod_data_source_block           I
_cod_depositor_comments
;
The following automatic conversions were performed:
'_geom_angle_publ_flag' value 'Y' changed to 'y' according to
'/home/saulius/struct/CIF-dictionaries/cif_core.dic' dictionary named
'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_enum 1527 2010-12-29 10:47:43Z saulius 

The following automatic conversions were performed:

'_geom_angle_publ_flag' value 'Y' changed to 'y' according to
/home/saulius/struct/CIF-dictionaries/cif_core.dic dictionary named
'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_database_code               2210973
_cod_database_fobs_code          2210973
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, z+1/2'
'-x+1/2, y, z+1/2'
'x+1/2, -y, 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_occupancy
C C1 0.66935(14) 0.6843(2) 0.4057(3) 0.0229(5) Uani d 1
C C2 0.57906(15) 0.5182(2) 0.3385(3) 0.0215(5) Uani d 1
C C3 0.66411(14) 0.4756(2) 0.2955(3) 0.0188(5) Uani d 1
C C4 0.69147(15) 0.3602(2) 0.2272(3) 0.0234(5) Uani d 1
H H4 0.6553(12) 0.294(2) 0.201(3) 0.019(6) Uiso d 1
C C5 0.77542(15) 0.3460(2) 0.2027(3) 0.0248(5) Uani d 1
H H5 0.7960(13) 0.265(2) 0.152(3) 0.030 Uiso d 1
C C6 0.82967(16) 0.4446(2) 0.2466(3) 0.0250(6) Uani d 1
H H6 0.8858(14) 0.431(2) 0.235(3) 0.021(6) Uiso d 1
C C7 0.80168(14) 0.5608(2) 0.3139(3) 0.0250(5) Uani d 1
H H7 0.8382(14) 0.629(2) 0.346(3) 0.030 Uiso d 1
C C8 0.71801(13) 0.5744(2) 0.3365(3) 0.0205(5) Uani d 1
C C9 0.51744(15) 0.7231(2) 0.4557(3) 0.0215(5) Uani d 1
H H9A 0.5370(14) 0.786(2) 0.546(3) 0.026 Uiso d 1
H H9B 0.4763(14) 0.663(2) 0.510(3) 0.026 Uiso d 1
C C10 0.48128(13) 0.7981(2) 0.3028(3) 0.0190(5) Uani d 1
C C11 0.42115(13) 0.8902(2) 0.3390(3) 0.0201(5) Uani d 1
C C12 0.38795(15) 0.9654(2) 0.2042(3) 0.0221(5) Uani d 1
H H12 0.3446(15) 1.033(2) 0.236(3) 0.027 Uiso d 1
C C13 0.41287(14) 0.9436(2) 0.0306(3) 0.0261(6) Uani d 1
H H13 0.3863(17) 0.998(3) -0.065(4) 0.045(8) Uiso d 1
C C14 0.46871(15) 0.8491(2) -0.0091(3) 0.0271(6) Uani d 1
H H14 0.4906(16) 0.829(2) -0.128(4) 0.041(8) Uiso d 1
C C15 0.50330(15) 0.7772(2) 0.1285(3) 0.0237(6) Uani d 1
H H15 0.5470(16) 0.708(2) 0.100(3) 0.034(7) Uiso d 1
C C16 0.33043(18) 0.9828(3) 0.5524(4) 0.0342(7) Uani d 1
H H16A 0.3467(16) 1.078(3) 0.525(4) 0.049(8) Uiso d 1
H H16B 0.3201(16) 0.974(2) 0.673(4) 0.037(8) Uiso d 1
H H16C 0.2782(16) 0.958(2) 0.484(4) 0.043(8) Uiso d 1
N N1 0.58714(11) 0.64334(17) 0.4043(2) 0.0214(5) Uani d 1
O O1 0.69239(11) 0.78846(15) 0.4549(2) 0.0314(4) Uani d 1
O O2 0.51491(10) 0.46103(14) 0.3235(2) 0.0283(4) Uani d 1
O O3 0.39815(9) 0.89962(15) 0.5138(2) 0.0242(4) Uani 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
_geom_angle_publ_flag
O1 C1 N1 124.9(2) ?
O1 C1 C8 129.4(2) ?
N1 C1 C8 105.70(18) ?
O2 C2 N1 125.0(2) ?
O2 C2 C3 129.5(2) ?
N1 C2 C3 105.5(2) ?
C4 C3 C8 121.7(2) ?
C4 C3 C2 129.8(2) ?
C8 C3 C2 108.49(19) ?
C3 C4 C5 117.4(2) ?
C3 C4 H4 121.4(13) ?
C5 C4 H4 121.2(13) ?
C4 C5 C6 120.9(2) ?
C4 C5 H5 118.5(13) ?
C6 C5 H5 120.6(13) ?
C7 C6 C5 121.4(2) ?
C7 C6 H6 119.4(14) ?
C5 C6 H6 119.1(14) ?
C8 C7 C6 117.3(2) ?
C8 C7 H7 120.5(14) ?
C6 C7 H7 122.2(14) ?
C7 C8 C3 121.3(2) ?
C7 C8 C1 130.4(2) ?
C3 C8 C1 108.26(18) ?
N1 C9 C10 113.15(18) y
N1 C9 H9A 107.9(13) ?
C10 C9 H9A 108.1(13) ?
N1 C9 H9B 105.8(13) ?
C10 C9 H9B 112.0(13) ?
H9A C9 H9B 109.8(19) ?
C15 C10 C11 118.5(2) ?
C15 C10 C9 123.0(2) ?
C11 C10 C9 118.48(19) ?
O3 C11 C12 123.7(2) ?
O3 C11 C10 115.32(18) ?
C12 C11 C10 120.9(2) ?
C13 C12 C11 118.9(2) ?
C13 C12 H12 122.0(14) ?
C11 C12 H12 119.0(14) ?
C14 C13 C12 121.0(2) ?
C14 C13 H13 121.9(16) ?
C12 C13 H13 117.0(16) ?
C13 C14 C15 119.2(2) ?
C13 C14 H14 126.2(16) ?
C15 C14 H14 114.5(16) ?
C10 C15 C14 121.3(2) ?
C10 C15 H15 119.2(14) ?
C14 C15 H15 119.5(14) ?
O3 C16 H16A 109.8(15) ?
O3 C16 H16B 106.2(17) ?
H16A C16 H16B 109(2) ?
O3 C16 H16C 112.5(15) ?
H16A C16 H16C 110(2) ?
H16B C16 H16C 109(2) ?
C2 N1 C1 112.01(19) ?
C2 N1 C9 123.5(2) ?
C1 N1 C9 124.42(18) ?
C11 O3 C16 116.62(19) ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C1 O1 1.208(3)
C1 N1 1.405(3)
C1 C8 1.488(3)
C2 O2 1.208(3)
C2 N1 1.403(3)
C2 C3 1.490(3)
C3 C4 1.383(3)
C3 C8 1.389(3)
C4 C5 1.387(3)
C4 H4 0.93(2)
C5 C6 1.396(3)
C5 H5 0.99(2)
C6 C7 1.390(3)
C6 H6 0.93(2)
C7 C8 1.380(3)
C7 H7 0.95(2)
C9 N1 1.460(3)
C9 C10 1.514(3)
C9 H9A 1.00(2)
C9 H9B 1.01(2)
C10 C15 1.382(3)
C10 C11 1.399(3)
C11 O3 1.377(3)
C11 C12 1.395(3)
C12 C13 1.392(4)
C12 H12 1.03(2)
C13 C14 1.374(3)
C13 H13 1.02(3)
C14 C15 1.400(3)
C14 H14 0.99(3)
C15 H15 1.04(3)
C16 O3 1.433(3)
C16 H16A 1.05(3)
C16 H16B 0.93(3)
C16 H16C 1.03(3)
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
_geom_hbond_publ_flag
C6 H6 O2 4_565 0.93(2) 2.48(2) 3.225(3) 137.7(17) y
C13 H13 O1 2_674 1.02(3) 2.57(3) 3.327(3) 131(2) y
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_publ_flag
C8 C1 N1 C9 -177.60(18) ?
C3 C2 N1 C9 177.33(18) ?
C10 C9 N1 C1 89.8(2) y
C10 C9 N1 C2 -86.7(2) y
N1 C9 C10 C11 -171.95(19) y
N1 C9 C10 C15 9.9(3) y
C10 C11 O3 C16 -173.3(2) y
C12 C11 O3 C16 6.5(3) y
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 840269
