#------------------------------------------------------------------------------
#$Date: 2017-10-13 03:48:21 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201957 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/01/32/2013258.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_2013258
loop_
_publ_author_name
'Dey, Sankar Prasad'
'Dey, Dilip Kumar'
'Mallik, Asok Kumar'
'Dahlenburg, Lutz'
_publ_section_title
;
 6-(2-Hydroxybenzoyl)-5-(pyrrol-2-yl)-3H-pyrrolizine
;
_journal_issue                   6
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              o321
_journal_page_last               o322
_journal_paper_doi               10.1107/S0108270103008394
_journal_volume                  59
_journal_year                    2003
_chemical_formula_iupac          'C18 H14 N2 O2'
_chemical_formula_moiety         'C18 H14 N2 O2'
_chemical_formula_sum            'C18 H14 N2 O2'
_chemical_formula_weight         290.31
_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'
_audit_creation_method           'WinGX routine CIF_UPDATE'
_cell_angle_alpha                90
_cell_angle_beta                 104.407(16)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   8.6868(7)
_cell_length_b                   22.0328(13)
_cell_length_c                   7.592(3)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      12.7
_cell_measurement_theta_min      8.4
_cell_volume                     1407.4(6)
_computing_cell_refinement       'CAD-4 EXPRESS'
_computing_data_collection       'CAD-4 EXPRESS (Enraf-Nonius, 1994)'
_computing_data_reduction        'XCAD4 (Harms & Wocadlo, 1995)'
_computing_molecular_graphics    'ORTEP-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX (Farrugia, 1999)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SIR97 (Altomare et al., 1999)'
_diffrn_measured_fraction_theta_full 0.989
_diffrn_measured_fraction_theta_max 0.989
_diffrn_measurement_device       'κ-geometry diffractometer'
_diffrn_measurement_device_type  'Nonius MACH3'
_diffrn_measurement_method       'non-profiled ω'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0222
_diffrn_reflns_limit_h_max       0
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       0
_diffrn_reflns_limit_k_min       -26
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_number            2666
_diffrn_reflns_theta_full        25.18
_diffrn_reflns_theta_max         25.18
_diffrn_reflns_theta_min         2.42
_diffrn_standards_decay_%        1
_diffrn_standards_interval_time  60
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    0.091
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            red
_exptl_crystal_density_diffrn    1.37
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             608
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.153
_refine_diff_density_min         -0.148
_refine_ls_extinction_coef       0.0134(19)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL97
_refine_ls_goodness_of_fit_ref   1.027
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     208
_refine_ls_number_reflns         2499
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.027
_refine_ls_R_factor_gt           0.043
_refine_ls_shift/su_max          0
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w = 1/[σ²(Fo²)+(0.0518P)²+0.2924P] where P = (Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_ref         0.1131
_reflns_number_gt                1796
_reflns_number_total             2499
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            fa1012.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2013258
_cod_database_fobs_code          2013258
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_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
_atom_site_disorder_assembly
_atom_site_disorder_group
_atom_site_type_symbol
O1 0.2536(2) 0.50797(7) 0.7283(2) 0.0690(5) Uani d . 1 . . O
H1 0.161(3) 0.5270(12) 0.647(4) 0.091(9) Uiso d . 1 . . H
O2 0.07854(17) 0.58247(6) 0.5012(2) 0.0661(5) Uani d . 1 . . O
N1 0.06924(18) 0.77490(7) 0.4304(2) 0.0422(4) Uani d . 1 . . N
N2 -0.1586(2) 0.63674(8) 0.2532(2) 0.0499(4) Uani d . 1 . . N
H2 -0.095(3) 0.6067(10) 0.316(3) 0.071(7) Uiso d . 1 . . H
C1 0.2415(3) 0.84817(9) 0.5684(3) 0.0533(5) Uani d . 1 . . C
H1A 0.3316 0.8669 0.6397 0.064 Uiso calc R 1 . . H
C2 0.1133(3) 0.87640(9) 0.4716(3) 0.0561(6) Uani d . 1 . . C
H2A 0.1012 0.9183 0.4662 0.067 Uiso calc R 1 . . H
C3 -0.0092(2) 0.83267(8) 0.3725(3) 0.0479(5) Uani d . 1 . . C
H3A -0.1078 0.8365 0.4096 0.058 Uiso calc R 1 . . H
H3B -0.0303 0.8379 0.2418 0.058 Uiso calc R 1 . . H
C4 0.0345(2) 0.71511(8) 0.4028(3) 0.0404(4) Uani d . 1 . . C
C5 0.1710(2) 0.68353(8) 0.5034(3) 0.0429(5) Uani d . 1 . . C
C6 0.2843(2) 0.72810(9) 0.5914(3) 0.0468(5) Uani d . 1 . . C
H6 0.3845 0.7205 0.6665 0.056 Uiso calc R 1 . . H
C7 0.2181(2) 0.78346(8) 0.5448(3) 0.0450(5) Uani d . 1 . . C
C8 -0.1146(2) 0.69644(8) 0.2830(3) 0.0418(5) Uani d . 1 . . C
C9 -0.2356(2) 0.73019(9) 0.1742(3) 0.0520(5) Uani d . 1 . . C
H9 -0.2395 0.7723 0.1656 0.062 Uiso calc R 1 . . H
C10 -0.3511(2) 0.68993(10) 0.0794(3) 0.0563(6) Uani d . 1 . . C
H10 -0.4453 0.7004 -0.0038 0.068 Uiso calc R 1 . . H
C11 -0.3007(2) 0.63267(10) 0.1309(3) 0.0574(6) Uani d . 1 . . C
H11 -0.3547 0.597 0.0891 0.069 Uiso calc R 1 . . H
C12 0.3772(3) 0.53855(9) 0.6903(3) 0.0531(5) Uani d . 1 . . C
C13 0.5280(3) 0.51433(10) 0.7530(3) 0.0656(7) Uani d . 1 . . C
H13 0.5428 0.4798 0.8258 0.079 Uiso calc R 1 . . H
C14 0.6553(3) 0.54105(11) 0.7084(4) 0.0702(7) Uani d . 1 . . C
H14 0.7559 0.5241 0.7496 0.084 Uiso calc R 1 . . H
C15 0.6363(3) 0.59277(11) 0.6029(3) 0.0622(6) Uani d . 1 . . C
H15 0.7228 0.6099 0.5696 0.075 Uiso calc R 1 . . H
C16 0.4879(2) 0.61888(9) 0.5472(3) 0.0527(5) Uani d . 1 . . C
H16 0.4756 0.6543 0.4785 0.063 Uiso calc R 1 . . H
C17 0.3557(2) 0.59318(9) 0.5919(3) 0.0469(5) Uani d . 1 . . C
C18 0.1938(2) 0.61877(9) 0.5279(3) 0.0482(5) Uani d . 1 . . C
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 0 '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 0.006 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_diffrn_standard_refln_index_h
_diffrn_standard_refln_index_k
_diffrn_standard_refln_index_l
-1 -9 -1
-1 -10 -1
4 5 -2
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
C12 O1 H1 102.9(15) ?
C4 N1 C7 111.59(15) y
C4 N1 C3 137.01(16) y
C7 N1 C3 111.40(15) y
C11 N2 C8 110.24(18) y
C11 N2 H2 129.6(15) ?
C8 N2 H2 120.1(14) ?
C2 C1 C7 108.72(19) y
C2 C1 H1A 125.6 ?
C7 C1 H1A 125.6 ?
C1 C2 C3 111.82(18) y
C1 C2 H2A 124.1 ?
C3 C2 H2A 124.1 ?
N1 C3 C2 100.95(16) y
N1 C3 H3A 111.6 ?
C2 C3 H3A 111.6 ?
N1 C3 H3B 111.6 ?
C2 C3 H3B 111.6 ?
H3A C3 H3B 109.4 ?
N1 C4 C5 105.56(16) y
N1 C4 C8 120.28(16) y
C5 C4 C8 134.09(17) y
C4 C5 C6 107.42(16) y
C4 C5 C18 128.38(17) y
C6 C5 C18 124.08(17) y
C7 C6 C5 107.30(17) y
C7 C6 H6 126.3 ?
C5 C6 H6 126.3 ?
C6 C7 N1 108.12(16) y
C6 C7 C1 144.8(2) y
N1 C7 C1 107.09(17) y
N2 C8 C9 106.17(17) y
N2 C8 C4 123.06(17) y
C9 C8 C4 130.74(18) y
C8 C9 C10 107.96(18) y
C8 C9 H9 126 ?
C10 C9 H9 126 ?
C11 C10 C9 107.59(19) y
C11 C10 H10 126.2 ?
C9 C10 H10 126.2 ?
N2 C11 C10 108.04(19) y
N2 C11 H11 126 ?
C10 C11 H11 126 ?
O1 C12 C13 117.8(2) ?
O1 C12 C17 122.03(18) ?
C13 C12 C17 120.2(2) ?
C14 C13 C12 120.2(2) ?
C14 C13 H13 119.9 ?
C12 C13 H13 119.9 ?
C13 C14 C15 120.8(2) ?
C13 C14 H14 119.6 ?
C15 C14 H14 119.6 ?
C16 C15 C14 119.4(2) ?
C16 C15 H15 120.3 ?
C14 C15 H15 120.3 ?
C15 C16 C17 121.3(2) ?
C15 C16 H16 119.4 ?
C17 C16 H16 119.4 ?
C16 C17 C12 117.93(19) ?
C16 C17 C18 122.51(18) ?
C12 C17 C18 119.40(18) ?
O2 C18 C5 121.90(18) y
O2 C18 C17 117.63(17) y
C5 C18 C17 120.43(17) y
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
O1 C12 . 1.358(3) y
O1 H1 . 0.98(3) ?
O2 C18 . 1.258(2) y
N1 C4 . 1.356(2) y
N1 C7 . 1.380(2) y
N1 C3 . 1.459(2) y
N2 C11 . 1.351(3) y
N2 C8 . 1.373(2) y
N2 H2 . 0.91(2) ?
C1 C2 . 1.327(3) y
C1 C7 . 1.445(3) y
C1 H1A . 0.93 ?
C2 C3 . 1.493(3) y
C2 H2A . 0.93 ?
C3 H3A . 0.97 ?
C3 H3B . 0.97 ?
C4 C5 . 1.422(3) y
C4 C8 . 1.445(3) y
C5 C6 . 1.432(3) y
C5 C18 . 1.446(3) y
C6 C7 . 1.357(3) y
C6 H6 . 0.93 ?
C8 C9 . 1.381(3) y
C9 C10 . 1.397(3) y
C9 H9 . 0.93 ?
C10 C11 . 1.360(3) y
C10 H10 . 0.93 ?
C11 H11 . 0.93 ?
C12 C13 . 1.385(3) ?
C12 C17 . 1.404(3) ?
C13 C14 . 1.368(3) ?
C13 H13 . 0.93 ?
C14 C15 . 1.379(3) ?
C14 H14 . 0.93 ?
C15 C16 . 1.378(3) ?
C15 H15 . 0.93 ?
C16 C17 . 1.396(3) ?
C16 H16 . 0.93 ?
C17 C18 . 1.481(3) y
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
O1 H1 O2 0.98(3) 1.68(3) 2.584(2) 151(2)
N2 H2 O2 0.91(2) 1.87(2) 2.699(2) 150(2)
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
C7 C1 C2 C3 -0.2(2) ?
C4 N1 C3 C2 178.4(2) ?
C7 N1 C3 C2 -1.0(2) ?
C1 C2 C3 N1 0.7(2) ?
C7 N1 C4 C5 -1.1(2) ?
C3 N1 C4 C5 179.5(2) ?
C7 N1 C4 C8 -178.35(16) ?
C3 N1 C4 C8 2.2(3) ?
N1 C4 C5 C6 0.7(2) ?
C8 C4 C5 C6 177.45(19) ?
N1 C4 C5 C18 176.70(19) ?
C8 C4 C5 C18 -6.6(3) ?
C4 C5 C6 C7 -0.1(2) ?
C18 C5 C6 C7 -176.33(19) ?
C5 C6 C7 N1 -0.5(2) ?
C5 C6 C7 C1 178.9(3) ?
C4 N1 C7 C6 1.0(2) ?
C3 N1 C7 C6 -179.39(16) ?
C4 N1 C7 C1 -178.63(16) ?
C3 N1 C7 C1 1.0(2) ?
C2 C1 C7 C6 -179.9(3) ?
C2 C1 C7 N1 -0.5(2) ?
C11 N2 C8 C9 0.1(2) ?
C11 N2 C8 C4 -177.92(18) ?
N1 C4 C8 N2 -178.23(17) y
C5 C4 C8 N2 5.4(3) n
N1 C4 C8 C9 4.2(3) n
C5 C4 C8 C9 -172.1(2) n
N2 C8 C9 C10 -0.2(2) ?
C4 C8 C9 C10 177.63(19) ?
C8 C9 C10 C11 0.2(2) ?
C8 N2 C11 C10 0.0(2) ?
C9 C10 C11 N2 -0.1(2) ?
O1 C12 C13 C14 175.6(2) ?
C17 C12 C13 C14 -4.8(3) ?
C12 C13 C14 C15 0.9(4) ?
C13 C14 C15 C16 2.2(3) ?
C14 C15 C16 C17 -1.5(3) ?
C15 C16 C17 C12 -2.2(3) ?
C15 C16 C17 C18 -177.46(19) ?
O1 C12 C17 C16 -175.09(18) ?
C13 C12 C17 C16 5.3(3) ?
O1 C12 C17 C18 0.3(3) ?
C13 C12 C17 C18 -179.26(19) ?
C4 C5 C18 O2 -19.5(3) ?
C6 C5 C18 O2 155.9(2) ?
C4 C5 C18 C17 162.63(19) y
C6 C5 C18 C17 -22.0(3) n
C16 C17 C18 O2 148.9(2) ?
C12 C17 C18 O2 -26.3(3) ?
C16 C17 C18 C5 -33.1(3) n
C12 C17 C18 C5 151.64(19) n
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 9464259
