#------------------------------------------------------------------------------
#$Date: 2016-02-18 17:37:37 +0200 (Thu, 18 Feb 2016) $
#$Revision: 176729 $
#$URL: svn://www.crystallography.net/cod/cif/1/50/56/1505630.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_1505630
loop_
_publ_author_name
'Vacas, Tatiana'
'Alvarez, Eleuterio'
'Chiara, Jose Luis'
_publ_section_title
;
 Phthalimides as exceptionally efficient single electron transfer
 acceptors in reductive coupling reactions promoted by samarium diiodide.
;
_journal_issue                   26
_journal_name_full               'Organic letters'
_journal_page_first              5445
_journal_page_last               5448
_journal_paper_doi               10.1021/ol7023357
_journal_volume                  9
_journal_year                    2007
_chemical_formula_moiety         'C19 H20 N2 O3'
_chemical_formula_sum            'C19 H20 N2 O3'
_chemical_formula_weight         324.37
_chemical_name_systematic
; 
 ? 
;
_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                 99.448(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   7.3633(3)
_cell_length_b                   15.3041(6)
_cell_length_c                   14.7261(6)
_cell_measurement_reflns_used    7609
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      30.68
_cell_measurement_theta_min      2.66
_cell_volume                     1636.95(11)
_computing_cell_refinement       'SAINT+ v. 7.06 a (Bruker AXS, 2003)'
_computing_data_collection       'APEX-W2K-NT v. 1.0 (Bruker AXS, 2004)'
_computing_data_reduction        'SAINT+ v. 7.06 a (Bruker AXS, 2001)'
_computing_molecular_graphics    'XP, SHELXTL v. 6.10 (Bruker, 2000)'
_computing_publication_material  'XCIF, SHELXTL v. 6.12 (Bruker, 2001)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean 8.26
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device_type
;
 Bruker-Nonius X8kappa APEX II CCD area detector'
;
_diffrn_measurement_method       'phi and omega scans with narrow frames'
_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  0.0414
_diffrn_reflns_av_sigmaI/netI    0.0288
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            74385
_diffrn_reflns_theta_full        30.89
_diffrn_reflns_theta_max         30.89
_diffrn_reflns_theta_min         2.80
_diffrn_standards_decay_%        0
_exptl_absorpt_coefficient_mu    0.090
_exptl_absorpt_correction_T_max  0.9779
_exptl_absorpt_correction_T_min  0.9497
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
; 
 SADABS v. 2.03: Area-Detector Absorption Correction.
 (1997-2001) Bruker-AXS within SAINT+ package, v. 6.04
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.316
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             688
_exptl_crystal_size_max          0.58
_exptl_crystal_size_mid          0.57
_exptl_crystal_size_min          0.25
_refine_diff_density_max         0.464
_refine_diff_density_min         -0.389
_refine_diff_density_rms         0.069
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.084
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     224
_refine_ls_number_reflns         5147
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.084
_refine_ls_R_factor_all          0.0743
_refine_ls_R_factor_gt           0.0467
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0470P)²+1.1527P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1085
_refine_ls_wR_factor_ref         0.1276
_reflns_number_gt                3827
_reflns_number_total             5147
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol7023357-file003.cif
_cod_data_source_block           8_minor_diastereoisomer
_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_original_sg_symbol_H-M      P2(1)/c
_cod_database_code               1505630
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_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
O1 O 1.02498(14) -0.24840(6) 0.72089(7) 0.0209(2) Uani 1 1 d .
O2 O 1.05742(14) 0.00130(7) 0.88856(7) 0.0178(2) Uani 1 1 d .
H2 H 0.982(3) 0.0389(13) 0.9069(13) 0.021 Uiso 1 1 d .
O3 O 0.71877(15) 0.12047(7) 0.77557(7) 0.0193(2) Uani 1 1 d .
H3 H 0.798(3) 0.1609(13) 0.8005(13) 0.023 Uiso 1 1 d .
N1 N 0.71624(15) 0.06006(7) 0.85120(8) 0.0143(2) Uani 1 1 d .
N4 N 0.97269(16) -0.13434(7) 0.81555(8) 0.0160(2) Uani 1 1 d .
C1 C 0.74306(17) -0.02767(8) 0.81414(9) 0.0135(2) Uani 1 1 d .
C2 C 0.71756(19) -0.09797(9) 0.88651(10) 0.0185(3) Uani 1 1 d .
H2A H 0.7577 -0.0755 0.9497 0.022 Uiso 1 1 calc R
H2B H 0.5870 -0.1160 0.8801 0.022 Uiso 1 1 calc R
C3 C 0.8391(2) -0.17510(9) 0.86634(10) 0.0206(3) Uani 1 1 d .
H3A H 0.9017 -0.2023 0.9241 0.025 Uiso 1 1 calc R
H3B H 0.7654 -0.2201 0.8285 0.025 Uiso 1 1 calc R
C5 C 1.02735(18) -0.16980(9) 0.73958(9) 0.0162(3) Uani 1 1 d .
C5A C 1.08007(18) -0.09610(9) 0.68435(9) 0.0152(2) Uani 1 1 d .
C6 C 1.16352(19) -0.09775(10) 0.60632(9) 0.0186(3) Uani 1 1 d .
H6 H 1.1944 -0.1513 0.5801 0.022 Uiso 1 1 calc R
C7 C 1.2000(2) -0.01789(10) 0.56822(10) 0.0216(3) Uani 1 1 d .
H7 H 1.2560 -0.0164 0.5146 0.026 Uiso 1 1 calc R
C8 C 1.1547(2) 0.06009(10) 0.60825(10) 0.0207(3) Uani 1 1 d .
H8 H 1.1815 0.1140 0.5813 0.025 Uiso 1 1 calc R
C9 C 1.07126(19) 0.06122(9) 0.68679(10) 0.0175(3) Uani 1 1 d .
H9 H 1.0419 0.1147 0.7138 0.021 Uiso 1 1 calc R
C9A C 1.03279(17) -0.01851(9) 0.72395(9) 0.0141(2) Uani 1 1 d .
C10 C 0.95379(18) -0.03884(8) 0.81025(9) 0.0136(2) Uani 1 1 d .
C11 C 0.62245(19) -0.04710(10) 0.72198(10) 0.0197(3) Uani 1 1 d .
H11A H 0.4925 -0.0413 0.7283 0.029 Uiso 1 1 calc R
H11B H 0.6461 -0.1068 0.7028 0.029 Uiso 1 1 calc R
H11C H 0.6512 -0.0057 0.6756 0.029 Uiso 1 1 calc R
C12 C 0.53645(18) 0.07310(9) 0.88066(10) 0.0183(3) Uani 1 1 d .
H12A H 0.5107 0.0233 0.9195 0.022 Uiso 1 1 calc R
H12B H 0.4386 0.0749 0.8259 0.022 Uiso 1 1 calc R
C13 C 0.53414(18) 0.15686(9) 0.93411(9) 0.0165(3) Uani 1 1 d .
C14 C 0.67247(19) 0.17533(9) 1.00854(10) 0.0181(3) Uani 1 1 d .
H14 H 0.7727 0.1360 1.0237 0.022 Uiso 1 1 calc R
C15 C 0.6649(2) 0.25054(10) 1.06048(10) 0.0196(3) Uani 1 1 d .
H15 H 0.7601 0.2626 1.1108 0.024 Uiso 1 1 calc R
C16 C 0.5180(2) 0.30846(10) 1.03903(10) 0.0206(3) Uani 1 1 d .
H16 H 0.5122 0.3598 1.0747 0.025 Uiso 1 1 calc R
C17 C 0.3804(2) 0.29054(10) 0.96520(10) 0.0222(3) Uani 1 1 d .
H17 H 0.2801 0.3298 0.9503 0.027 Uiso 1 1 calc R
C18 C 0.3884(2) 0.21532(10) 0.91278(9) 0.0202(3) Uani 1 1 d .
H18 H 0.2938 0.2038 0.8621 0.024 Uiso 1 1 calc R
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
C10 O2 H2 104.8(12)
N1 O3 H3 102.5(12)
O3 N1 C12 105.39(10)
O3 N1 C1 106.07(9)
C12 N1 C1 114.44(10)
C5 N4 C3 124.18(12)
C5 N4 C10 113.01(11)
C3 N4 C10 112.59(11)
N1 C1 C11 114.41(11)
N1 C1 C2 109.84(10)
C11 C1 C2 111.03(11)
N1 C1 C10 107.79(10)
C11 C1 C10 112.39(11)
C2 C1 C10 100.46(10)
C3 C2 C1 105.07(11)
C3 C2 H2A 110.7
C1 C2 H2A 110.7
C3 C2 H2B 110.7
C1 C2 H2B 110.7
H2A C2 H2B 108.8
N4 C3 C2 103.40(11)
N4 C3 H3A 111.1
C2 C3 H3A 111.1
N4 C3 H3B 111.1
C2 C3 H3B 111.1
H3A C3 H3B 109.0
O1 C5 N4 125.21(13)
O1 C5 C5A 128.04(13)
N4 C5 C5A 106.70(11)
C6 C5A C9A 122.47(13)
C6 C5A C5 129.24(12)
C9A C5A C5 108.29(11)
C7 C6 C5A 117.32(13)
C7 C6 H6 121.3
C5A C6 H6 121.3
C6 C7 C8 120.44(13)
C6 C7 H7 119.8
C8 C7 H7 119.8
C7 C8 C9 121.91(13)
C7 C8 H8 119.0
C9 C8 H8 119.0
C9A C9 C8 117.56(13)
C9A C9 H9 121.2
C8 C9 H9 121.2
C9 C9A C5A 120.29(12)
C9 C9A C10 130.10(12)
C5A C9A C10 109.46(11)
O2 C10 N4 110.80(10)
O2 C10 C9A 111.40(10)
N4 C10 C9A 101.71(10)
O2 C10 C1 109.08(10)
N4 C10 C1 101.06(10)
C9A C10 C1 121.72(11)
C1 C11 H11A 109.5
C1 C11 H11B 109.5
H11A C11 H11B 109.5
C1 C11 H11C 109.5
H11A C11 H11C 109.5
H11B C11 H11C 109.5
N1 C12 C13 110.92(11)
N1 C12 H12A 109.5
C13 C12 H12A 109.5
N1 C12 H12B 109.5
C13 C12 H12B 109.5
H12A C12 H12B 108.0
C18 C13 C14 118.84(13)
C18 C13 C12 120.22(13)
C14 C13 C12 120.87(12)
C15 C14 C13 120.68(13)
C15 C14 H14 119.7
C13 C14 H14 119.7
C14 C15 C16 120.14(13)
C14 C15 H15 119.9
C16 C15 H15 119.9
C17 C16 C15 119.46(14)
C17 C16 H16 120.3
C15 C16 H16 120.3
C16 C17 C18 120.42(13)
C16 C17 H17 119.8
C18 C17 H17 119.8
C13 C18 C17 120.47(13)
C13 C18 H18 119.8
C17 C18 H18 119.8
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O1 C5 1.2335(17)
O2 C10 1.4143(16)
O2 H2 0.87(2)
O3 N1 1.4500(14)
O3 H3 0.89(2)
N1 C12 1.4728(17)
N1 C1 1.4748(17)
N4 C5 1.3623(17)
N4 C3 1.4687(18)
N4 C10 1.4690(17)
C1 C11 1.5242(19)
C1 C2 1.5473(18)
C1 C10 1.5714(18)
C2 C3 1.539(2)
C2 H2A 0.9900
C2 H2B 0.9900
C3 H3A 0.9900
C3 H3B 0.9900
C5 C5A 1.4792(19)
C5A C6 1.3894(19)
C5A C9A 1.3921(18)
C6 C7 1.389(2)
C6 H6 0.9500
C7 C8 1.395(2)
C7 H7 0.9500
C8 C9 1.396(2)
C8 H8 0.9500
C9 C9A 1.3854(19)
C9 H9 0.9500
C9A C10 1.5144(18)
C11 H11A 0.9800
C11 H11B 0.9800
C11 H11C 0.9800
C12 C13 1.5058(19)
C12 H12A 0.9900
C12 H12B 0.9900
C13 C18 1.3927(19)
C13 C14 1.3972(19)
C14 C15 1.388(2)
C14 H14 0.9500
C15 C16 1.394(2)
C15 H15 0.9500
C16 C17 1.386(2)
C16 H16 0.9500
C17 C18 1.393(2)
C17 H17 0.9500
C18 H18 0.9500
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O2 H2 N1 0.87(2) 2.023(19) 2.6398(15) 126.9(16) .
O3 H3 O1 0.89(2) 1.96(2) 2.7492(15) 146.6(17) 2_756
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
O3 N1 C1 C11 -47.17(13)
C12 N1 C1 C11 68.57(14)
O3 N1 C1 C2 -172.80(10)
C12 N1 C1 C2 -57.06(14)
O3 N1 C1 C10 78.63(11)
C12 N1 C1 C10 -165.64(11)
N1 C1 C2 C3 -151.55(11)
C11 C1 C2 C3 80.91(13)
C10 C1 C2 C3 -38.17(13)
C5 N4 C3 C2 -137.49(13)
C10 N4 C3 C2 5.10(15)
C1 C2 C3 N4 21.59(14)
C3 N4 C5 O1 -25.4(2)
C10 N4 C5 O1 -167.87(13)
C3 N4 C5 C5A 152.13(12)
C10 N4 C5 C5A 9.69(15)
O1 C5 C5A C6 -10.3(2)
N4 C5 C5A C6 172.21(13)
O1 C5 C5A C9A 170.08(14)
N4 C5 C5A C9A -7.38(14)
C9A C5A C6 C7 0.2(2)
C5 C5A C6 C7 -179.29(13)
C5A C6 C7 C8 0.5(2)
C6 C7 C8 C9 -0.4(2)
C7 C8 C9 C9A -0.5(2)
C8 C9 C9A C5A 1.2(2)
C8 C9 C9A C10 176.29(13)
C6 C5A C9A C9 -1.1(2)
C5 C5A C9A C9 178.50(12)
C6 C5A C9A C10 -177.14(12)
C5 C5A C9A C10 2.49(14)
C5 N4 C10 O2 -126.45(12)
C3 N4 C10 O2 86.65(13)
C5 N4 C10 C9A -7.94(14)
C3 N4 C10 C9A -154.84(11)
C5 N4 C10 C1 118.05(11)
C3 N4 C10 C1 -28.85(14)
C9 C9A C10 O2 -54.52(18)
C5A C9A C10 O2 120.98(12)
C9 C9A C10 N4 -172.60(13)
C5A C9A C10 N4 2.90(14)
C9 C9A C10 C1 76.40(18)
C5A C9A C10 C1 -108.10(13)
N1 C1 C10 O2 37.92(13)
C11 C1 C10 O2 164.90(11)
C2 C1 C10 O2 -77.02(12)
N1 C1 C10 N4 154.69(10)
C11 C1 C10 N4 -78.33(13)
C2 C1 C10 N4 39.75(12)
N1 C1 C10 C9A -93.97(13)
C11 C1 C10 C9A 33.01(16)
C2 C1 C10 C9A 151.09(12)
O3 N1 C12 C13 -74.99(13)
C1 N1 C12 C13 168.88(11)
N1 C12 C13 C18 131.73(13)
N1 C12 C13 C14 -51.46(17)
C18 C13 C14 C15 0.1(2)
C12 C13 C14 C15 -176.75(12)
C13 C14 C15 C16 0.3(2)
C14 C15 C16 C17 -0.4(2)
C15 C16 C17 C18 0.0(2)
C14 C13 C18 C17 -0.4(2)
C12 C13 C18 C17 176.44(13)
C16 C17 C18 C13 0.4(2)
