#------------------------------------------------------------------------------
#$Date: 2019-11-28 20:06:24 +0200 (Thu, 28 Nov 2019) $
#$Revision: 244475 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/23/89/7238951.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_7238951
loop_
_publ_author_name
'Mahanta, Sanjeev P.'
'Panda, Pradeepta K.'
_publ_section_title
;
 Condensation of cyclohexanediones with pyrrole under acidic conditions:
 unusual products and interesting structural features
;
_journal_issue                   18
_journal_name_full               'RSC Adv.'
_journal_page_first              6614
_journal_paper_doi               10.1039/C3RA40208H
_journal_volume                  3
_journal_year                    2013
_chemical_formula_sum            'C14 H16 N2 O'
_chemical_formula_weight         228.29
_space_group_IT_number           60
_space_group_name_Hall           '-P 2n 2ab'
_space_group_name_H-M_alt        'P b c n'
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_H-M   'P b c n'
_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                   16.4455(8)
_cell_length_b                   7.7792(3)
_cell_length_c                   18.8199(9)
_cell_measurement_reflns_used    1732
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      28.8505
_cell_measurement_theta_min      2.6977
_cell_volume                     2407.68(19)
_computing_cell_refinement       CrysAlisPro
_computing_data_collection       CrysAlisPro
_computing_data_reduction        CrysAlisPro
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.868
_diffrn_measured_fraction_theta_max 0.868
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       '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  0.0351
_diffrn_reflns_av_sigmaI/netI    0.0610
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            6605
_diffrn_reflns_theta_full        28.92
_diffrn_reflns_theta_max         28.92
_diffrn_reflns_theta_min         2.90
_exptl_absorpt_coefficient_mu    0.081
_exptl_absorpt_correction_T_max  0.9912
_exptl_absorpt_correction_T_min  0.9888
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SCALE3 ABSPACK'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.260
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             976
_exptl_crystal_size_max          0.14
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.11
_refine_diff_density_max         0.131
_refine_diff_density_min         -0.182
_refine_diff_density_rms         0.039
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.002
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     162
_refine_ls_number_reflns         2766
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.002
_refine_ls_R_factor_all          0.1170
_refine_ls_R_factor_gt           0.0587
_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)+(0.0460P)²+0.1422P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1060
_refine_ls_wR_factor_ref         0.1285
_reflns_number_gt                1568
_reflns_number_total             2766
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c3ra40208h.txt
_cod_data_source_block           sanjib_s2
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_symmetry_cell_setting' value 'Orthorhombic' was changed
to 'orthorhombic' in accordance with the
/home/saulius/struct/COD-crude-data/automatic-downloads/DataCite-retrospective/RSC/depositions/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 last updated on
2011-04-26.

Automatic conversion script
Id: cif_fix_values 6909 2019-04-08 15:41:33Z antanas 
;
_cod_original_sg_symbol_H-M      'Pbcn '
_cod_database_code               7238951
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y+1/2, z+1/2'
'-x, y, -z+1/2'
'x+1/2, -y+1/2, -z'
'-x, -y, -z'
'x-1/2, y-1/2, -z-1/2'
'x, -y, z-1/2'
'-x-1/2, y-1/2, z'
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
N1 N 1.10048(11) 0.7294(2) 0.11236(10) 0.0439(5) Uani 1 1 d .
C9 C 0.92567(12) 0.8626(2) 0.14655(10) 0.0340(5) Uani 1 1 d .
C4 C 1.03056(12) 0.6380(2) 0.12437(10) 0.0359(5) Uani 1 1 d .
O1 O 0.86089(10) 0.93335(17) -0.04589(8) 0.0592(5) Uani 1 1 d .
N2 N 0.90792(13) 0.8469(2) 0.21696(10) 0.0550(6) Uani 1 1 d .
C5 C 0.94840(12) 0.7071(2) 0.10223(10) 0.0345(5) Uani 1 1 d .
C14 C 0.86893(13) 0.8086(2) -0.00723(11) 0.0434(5) Uani 1 1 d .
C11 C 0.95042(12) 0.7603(2) 0.02282(10) 0.0404(5) Uani 1 1 d .
H11A H 0.9870 0.8572 0.0175 0.049 Uiso 1 1 calc R
H11B H 0.9724 0.6657 -0.0047 0.049 Uiso 1 1 calc R
C10 C 0.88279(12) 0.5669(2) 0.11062(11) 0.0427(5) Uani 1 1 d .
H10A H 0.8979 0.4673 0.0826 0.051 Uiso 1 1 calc R
H10B H 0.8801 0.5316 0.1600 0.051 Uiso 1 1 calc R
C7 C 0.89100(14) 1.1188(2) 0.19240(12) 0.0513(6) Uani 1 1 d .
H7 H 0.8797 1.2356 0.1963 0.062 Uiso 1 1 calc R
C2 C 1.13780(14) 0.4946(3) 0.16900(13) 0.0527(6) Uani 1 1 d .
H2 H 1.1691 0.4111 0.1914 0.063 Uiso 1 1 calc R
C12 C 0.79996(13) 0.6294(2) 0.08720(11) 0.0493(6) Uani 1 1 d .
H12A H 0.7829 0.7230 0.1178 0.059 Uiso 1 1 calc R
H12B H 0.7609 0.5368 0.0923 0.059 Uiso 1 1 calc R
C8 C 0.91489(13) 1.0320(2) 0.13015(11) 0.0455(6) Uani 1 1 d .
H8 H 0.9221 1.0815 0.0856 0.055 Uiso 1 1 calc R
C1 C 1.16564(14) 0.6431(3) 0.13943(12) 0.0523(6) Uani 1 1 d .
H1 H 1.2195 0.6792 0.1380 0.063 Uiso 1 1 calc R
C3 C 1.05302(14) 0.4907(2) 0.15954(12) 0.0467(6) Uani 1 1 d .
H3 H 1.0182 0.4037 0.1745 0.056 Uiso 1 1 calc R
C13 C 0.80002(14) 0.6913(3) 0.01000(12) 0.0564(6) Uani 1 1 d .
H13A H 0.8025 0.5921 -0.0211 0.068 Uiso 1 1 calc R
H13B H 0.7493 0.7506 0.0005 0.068 Uiso 1 1 calc R
C6 C 0.88748(15) 1.0038(2) 0.24473(12) 0.0569(6) Uani 1 1 d .
H6 H 0.8736 1.0261 0.2917 0.068 Uiso 1 1 calc R
H1A H 1.1022(12) 0.832(2) 0.0918(11) 0.050(6) Uiso 1 1 d .
H2A H 0.9103(13) 0.751(3) 0.2409(14) 0.079(8) Uiso 1 1 d .
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
C1 N1 C4 110.02(17)
C1 N1 H1A 125.5(13)
C4 N1 H1A 124.4(13)
N2 C9 C8 106.19(17)
N2 C9 C5 121.07(16)
C8 C9 C5 132.68(18)
N1 C4 C3 106.65(18)
N1 C4 C5 121.31(15)
C3 C4 C5 132.00(18)
C9 N2 C6 110.09(17)
C9 N2 H2A 124.8(16)
C6 N2 H2A 125.1(16)
C4 C5 C9 110.62(16)
C4 C5 C10 110.21(14)
C9 C5 C10 109.60(16)
C4 C5 C11 109.95(16)
C9 C5 C11 108.80(14)
C10 C5 C11 107.60(16)
O1 C14 C13 122.3(2)
O1 C14 C11 121.32(18)
C13 C14 C11 116.33(17)
C14 C11 C5 114.22(17)
C14 C11 H11A 108.7
C5 C11 H11A 108.7
C14 C11 H11B 108.7
C5 C11 H11B 108.7
H11A C11 H11B 107.6
C12 C10 C5 111.88(14)
C12 C10 H10A 109.2
C5 C10 H10A 109.2
C12 C10 H10B 109.2
C5 C10 H10B 109.2
H10A C10 H10B 107.9
C6 C7 C8 107.77(17)
C6 C7 H7 126.1
C8 C7 H7 126.1
C1 C2 C3 107.47(19)
C1 C2 H2 126.3
C3 C2 H2 126.3
C10 C12 C13 112.17(19)
C10 C12 H12A 109.2
C13 C12 H12A 109.2
C10 C12 H12B 109.2
C13 C12 H12B 109.2
H12A C12 H12B 107.9
C9 C8 C7 108.13(18)
C9 C8 H8 125.9
C7 C8 H8 125.9
C2 C1 N1 107.8(2)
C2 C1 H1 126.1
N1 C1 H1 126.1
C4 C3 C2 108.03(18)
C4 C3 H3 126.0
C2 C3 H3 126.0
C14 C13 C12 113.55(18)
C14 C13 H13A 108.9
C12 C13 H13A 108.9
C14 C13 H13B 108.9
C12 C13 H13B 108.9
H13A C13 H13B 107.7
C7 C6 N2 107.81(19)
C7 C6 H6 126.1
N2 C6 H6 126.1
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
N1 C1 1.364(3)
N1 C4 1.371(2)
N1 H1A 0.885(19)
C9 N2 1.362(3)
C9 C8 1.365(2)
C9 C5 1.516(2)
C4 C3 1.374(2)
C4 C5 1.513(3)
O1 C14 1.220(2)
N2 C6 1.370(2)
N2 H2A 0.87(2)
C5 C10 1.543(3)
C5 C11 1.551(3)
C14 C13 1.490(3)
C14 C11 1.502(3)
C11 H11A 0.9700
C11 H11B 0.9700
C10 C12 1.512(3)
C10 H10A 0.9700
C10 H10B 0.9700
C7 C6 1.332(3)
C7 C8 1.408(3)
C7 H7 0.9300
C2 C1 1.361(3)
C2 C3 1.406(3)
C2 H2 0.9300
C12 C13 1.531(3)
C12 H12A 0.9700
C12 H12B 0.9700
C8 H8 0.9300
C1 H1 0.9300
C3 H3 0.9300
C13 H13A 0.9700
C13 H13B 0.9700
C6 H6 0.9300
