#------------------------------------------------------------------------------
#$Date: 2011-09-10 06:16:28 +0300 (Sat, 10 Sep 2011) $
#$Revision: 25271 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/2223376.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_2223376
loop_
_publ_author_name
'Gardu\~no-Beltr\'an, Olga'
'Rom\'an-Bravo, Perla'
'Medrano, Felipe'
'Tlahuext, Hugo'
_publ_section_title
;
N-(2-Pyridylmethyl)phthalimide
;
_journal_coeditor_code FL2266
_journal_issue 10
_journal_name_full 'Acta Crystallographica Section E'
_journal_page_first o2581
_journal_volume 65
_journal_year 2009
_chemical_formula_iupac 'C14 H10 N2 O2'
_chemical_formula_moiety 'C14 H10 N2 O2'
_chemical_formula_sum 'C14 H10 N2 O2'
_chemical_formula_weight 238.24
_chemical_melting_point 399
_chemical_name_systematic
;
N-(2-Pyridylmethyl)phthalimide
;
_space_group_IT_number 14
_symmetry_cell_setting monoclinic
_symmetry_space_group_name_Hall '-P 2ybc'
_symmetry_space_group_name_H-M 'P 1 21/c 1'
_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 106.373(3)
_cell_angle_gamma 90.00
_cell_formula_units_Z 4
_cell_length_a 11.7734(18)
_cell_length_b 14.239(2)
_cell_length_c 7.0698(11)
_cell_measurement_reflns_used 2665
_cell_measurement_temperature 293(2)
_cell_measurement_theta_max 26.81
_cell_measurement_theta_min 2.30
_cell_volume 1137.1(3)
_computing_cell_refinement 'SAINT-Plus-NT (Bruker, 2001)'
_computing_data_collection 'SMART (Bruker, 2000)'
_computing_data_reduction 'SAINT-Plus-NT (Bruker, 2001)'
_computing_molecular_graphics 'SHELXTL-NT (Sheldrick, 2008)'
_computing_publication_material
'PLATON (Spek, 2009) and publCIF (Westrip, 2009)'
_computing_structure_refinement 'SHELXTL-NT (Sheldrick, 2008)'
_computing_structure_solution 'SHELXTL-NT (Sheldrick, 2008)'
_diffrn_ambient_temperature 293(2)
_diffrn_detector_area_resol_mean 8.3
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type 'Bruker SMART APEX CCD area-detector'
_diffrn_measurement_method '\f and \w'
_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 0.0276
_diffrn_reflns_av_sigmaI/netI 0.0258
_diffrn_reflns_limit_h_max 13
_diffrn_reflns_limit_h_min -13
_diffrn_reflns_limit_k_max 16
_diffrn_reflns_limit_k_min -16
_diffrn_reflns_limit_l_max 8
_diffrn_reflns_limit_l_min -8
_diffrn_reflns_number 7150
_diffrn_reflns_theta_full 25.00
_diffrn_reflns_theta_max 25.00
_diffrn_reflns_theta_min 1.80
_diffrn_standards_number 0
_exptl_absorpt_coefficient_mu 0.095
_exptl_absorpt_correction_T_max 0.9821
_exptl_absorpt_correction_T_min 0.9583
_exptl_absorpt_correction_type multi-scan
_exptl_absorpt_process_details '(SADABS; Sheldrick, 1996)'
_exptl_crystal_colour colourless
_exptl_crystal_density_diffrn 1.392
_exptl_crystal_density_method 'not measured'
_exptl_crystal_description prism
_exptl_crystal_F_000 496
_exptl_crystal_size_max 0.45
_exptl_crystal_size_mid 0.28
_exptl_crystal_size_min 0.19
_refine_diff_density_max 0.181
_refine_diff_density_min -0.287
_refine_ls_extinction_method none
_refine_ls_goodness_of_fit_ref 1.198
_refine_ls_hydrogen_treatment constr
_refine_ls_matrix_type full
_refine_ls_number_parameters 163
_refine_ls_number_reflns 1994
_refine_ls_number_restraints 0
_refine_ls_restrained_S_all 1.198
_refine_ls_R_factor_all 0.0792
_refine_ls_R_factor_gt 0.0634
_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/[\s^2^(Fo^2^)+(0.0705P)^2^+0.1417P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme calc
_refine_ls_wR_factor_gt 0.1452
_refine_ls_wR_factor_ref 0.1550
_reflns_number_gt 1567
_reflns_number_total 1994
_reflns_threshold_expression I>2\s(I)
_[local]_cod_data_source_file fl2266.cif
_[local]_cod_data_source_block I
_[local]_cod_cif_authors_sg_H-M 'P 21/c'
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
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 2223376
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, 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_refinement_flags
_atom_site_occupancy
C C1 0.8978(2) 0.03798(15) 0.1337(3) 0.0493(6) Uani d . 1
C C2 1.01324(19) 0.07017(14) 0.2618(3) 0.0456(5) Uani d . 1
C C3 1.1103(2) 0.01983(16) 0.3657(3) 0.0533(6) Uani d . 1
H H3 1.1100 -0.0455 0.3665 0.064 Uiso calc R 1
C C4 1.2086(2) 0.07039(18) 0.4690(3) 0.0613(7) Uani d . 1
H H4 1.2760 0.0384 0.5399 0.074 Uiso calc R 1
C C5 1.2088(2) 0.16764(17) 0.4691(3) 0.0612(6) Uani d . 1
H H5 1.2761 0.1997 0.5405 0.073 Uiso calc R 1
C C6 1.1106(2) 0.21791(16) 0.3648(3) 0.0557(6) Uani d . 1
H H6 1.1105 0.2832 0.3646 0.067 Uiso calc R 1
C C7 1.01340(18) 0.16754(14) 0.2616(3) 0.0466(5) Uani d . 1
C C8 0.8971(2) 0.19976(15) 0.1347(3) 0.0515(6) Uani d . 1
C C9 0.7148(2) 0.11883(15) -0.0729(3) 0.0576(6) Uani d . 1
H H9A 0.7048 0.0621 -0.1517 0.069 Uiso calc R 1
H H9B 0.7075 0.1718 -0.1617 0.069 Uiso calc R 1
C C10 0.61635(19) 0.12393(13) 0.0243(3) 0.0484(6) Uani d . 1
C C11 0.6362(2) 0.13358(14) 0.2231(3) 0.0573(6) Uani d . 1
H H11 0.7128 0.1380 0.3066 0.069 Uiso calc R 1
C C12 0.5388(3) 0.13668(17) 0.2973(4) 0.0705(7) Uani d . 1
H H12 0.5489 0.1437 0.4319 0.085 Uiso calc R 1
C C13 0.4280(2) 0.12929(16) 0.1695(5) 0.0708(7) Uani d . 1
H H13 0.3614 0.1303 0.2156 0.085 Uiso calc R 1
C C14 0.4168(2) 0.12042(16) -0.0258(4) 0.0672(7) Uani d . 1
H H14 0.3410 0.1159 -0.1118 0.081 Uiso calc R 1
N N1 0.83334(16) 0.11904(11) 0.0626(3) 0.0530(5) Uani d . 1
N N2 0.50806(18) 0.11779(12) -0.1016(3) 0.0610(6) Uani d . 1
O O1 0.86171(15) -0.04110(11) 0.0924(2) 0.0652(5) Uani d . 1
O O2 0.85977(15) 0.27886(11) 0.0976(2) 0.0681(5) Uani d . 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
C1 0.0604(15) 0.0411(13) 0.0521(13) -0.0013(10) 0.0249(11) 0.0003(10)
C2 0.0532(13) 0.0419(12) 0.0483(12) 0.0033(10) 0.0251(10) 0.0040(9)
C3 0.0655(16) 0.0427(12) 0.0571(13) 0.0090(11) 0.0260(12) 0.0072(10)
C4 0.0564(15) 0.0678(17) 0.0592(14) 0.0082(12) 0.0154(12) 0.0116(12)
C5 0.0554(15) 0.0658(17) 0.0603(14) -0.0079(12) 0.0126(12) 0.0027(12)
C6 0.0610(15) 0.0447(13) 0.0630(14) -0.0036(11) 0.0201(12) 0.0014(11)
C7 0.0528(13) 0.0407(12) 0.0507(12) 0.0014(9) 0.0217(10) 0.0034(9)
C8 0.0566(14) 0.0404(13) 0.0608(14) 0.0018(10) 0.0218(11) 0.0040(10)
C9 0.0572(14) 0.0559(15) 0.0555(13) -0.0027(11) 0.0088(11) 0.0002(10)
C10 0.0528(13) 0.0335(12) 0.0540(12) 0.0012(9) 0.0069(10) 0.0016(9)
C11 0.0575(14) 0.0506(14) 0.0571(13) -0.0010(11) 0.0052(11) -0.0051(10)
C12 0.088(2) 0.0634(17) 0.0610(15) 0.0016(14) 0.0220(15) -0.0102(12)
C13 0.0612(16) 0.0625(17) 0.091(2) 0.0054(12) 0.0250(15) -0.0024(14)
C14 0.0513(15) 0.0626(17) 0.0794(18) -0.0002(11) 0.0050(13) 0.0013(13)
N1 0.0516(11) 0.0409(11) 0.0647(12) -0.0015(8) 0.0135(9) 0.0013(8)
N2 0.0555(12) 0.0563(13) 0.0627(12) -0.0001(9) 0.0029(10) 0.0025(9)
O1 0.0795(12) 0.0428(10) 0.0732(11) -0.0070(8) 0.0214(9) -0.0059(8)
O2 0.0689(11) 0.0409(10) 0.0873(12) 0.0063(8) 0.0100(9) 0.0071(8)
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 124.4(2)
O1 C1 C2 129.5(2)
N1 C1 C2 106.10(18)
C3 C2 C7 121.4(2)
C3 C2 C1 130.5(2)
C7 C2 C1 108.13(18)
C2 C3 C4 117.2(2)
C2 C3 H3 121.4
C4 C3 H3 121.4
C3 C4 C5 121.5(2)
C3 C4 H4 119.3
C5 C4 H4 119.3
C6 C5 C4 121.1(2)
C6 C5 H5 119.4
C4 C5 H5 119.4
C7 C6 C5 117.3(2)
C7 C6 H6 121.3
C5 C6 H6 121.3
C6 C7 C2 121.5(2)
C6 C7 C8 130.5(2)
C2 C7 C8 107.97(19)
O2 C8 N1 124.4(2)
O2 C8 C7 129.5(2)
N1 C8 C7 106.11(18)
N1 C9 C10 114.79(19)
N1 C9 H9A 108.6
C10 C9 H9A 108.6
N1 C9 H9B 108.6
C10 C9 H9B 108.6
H9A C9 H9B 107.5
N2 C10 C11 123.1(2)
N2 C10 C9 113.95(19)
C11 C10 C9 122.9(2)
C10 C11 C12 118.1(2)
C10 C11 H11 120.9
C12 C11 H11 120.9
C13 C12 C11 118.9(3)
C13 C12 H12 120.5
C11 C12 H12 120.5
C14 C13 C12 118.8(2)
C14 C13 H13 120.6
C12 C13 H13 120.6
N2 C14 C13 123.8(2)
N2 C14 H14 118.1
C13 C14 H14 118.1
C8 N1 C1 111.69(19)
C8 N1 C9 124.25(18)
C1 N1 C9 124.06(18)
C14 N2 C10 117.2(2)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C1 O1 1.210(3)
C1 N1 1.395(3)
C1 C2 1.477(3)
C2 C3 1.374(3)
C2 C7 1.386(3)
C3 C4 1.383(3)
C3 H3 0.9300
C4 C5 1.385(4)
C4 H4 0.9300
C5 C6 1.382(3)
C5 H5 0.9300
C6 C7 1.373(3)
C6 H6 0.9300
C7 C8 1.483(3)
C8 O2 1.210(2)
C8 N1 1.389(3)
C9 N1 1.453(3)
C9 C10 1.506(3)
C9 H9A 0.9700
C9 H9B 0.9700
C10 N2 1.336(3)
C10 C11 1.366(3)
C11 C12 1.391(3)
C11 H11 0.9300
C12 C13 1.365(4)
C12 H12 0.9300
C13 C14 1.356(4)
C13 H13 0.9300
C14 N2 1.329(3)
C14 H14 0.9300
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
C3 H3 O2 2_745 0.93 2.53 3.452(3) 171
C6 H6 O1 2_755 0.93 2.53 3.452(3) 171
C14 H14 O1 3_655 0.93 2.65 3.373(3) 134.9
C11 H11 O2 4_566 0.93 2.57 3.401(3) 148
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
O1 C1 C2 C3 0.9(4)
N1 C1 C2 C3 -178.73(19)
O1 C1 C2 C7 179.4(2)
N1 C1 C2 C7 -0.2(2)
C7 C2 C3 C4 -0.5(3)
C1 C2 C3 C4 177.91(19)
C2 C3 C4 C5 0.5(3)
C3 C4 C5 C6 -0.3(3)
C4 C5 C6 C7 0.0(3)
C5 C6 C7 C2 0.1(3)
C5 C6 C7 C8 -178.8(2)
C3 C2 C7 C6 0.2(3)
C1 C2 C7 C6 -178.53(18)
C3 C2 C7 C8 179.31(18)
C1 C2 C7 C8 0.6(2)
C6 C7 C8 O2 -2.5(4)
C2 C7 C8 O2 178.4(2)
C6 C7 C8 N1 178.2(2)
C2 C7 C8 N1 -0.8(2)
N1 C9 C10 N2 -176.06(17)
N1 C9 C10 C11 3.7(3)
N2 C10 C11 C12 0.3(3)
C9 C10 C11 C12 -179.42(19)
C10 C11 C12 C13 0.5(3)
C11 C12 C13 C14 -0.9(4)
C12 C13 C14 N2 0.5(4)
O2 C8 N1 C1 -178.6(2)
C7 C8 N1 C1 0.7(2)
O2 C8 N1 C9 2.3(3)
C7 C8 N1 C9 -178.38(18)
O1 C1 N1 C8 -180.0(2)
C2 C1 N1 C8 -0.3(2)
O1 C1 N1 C9 -0.9(3)
C2 C1 N1 C9 178.74(18)
C10 C9 N1 C8 -87.1(2)
C10 C9 N1 C1 93.9(2)
C13 C14 N2 C10 0.3(3)
C11 C10 N2 C14 -0.7(3)
C9 C10 N2 C14 179.06(18)