#------------------------------------------------------------------------------
#$Date: 2016-03-26 00:21:35 +0200 (Sat, 26 Mar 2016) $
#$Revision: 180074 $
#$URL: svn://www.crystallography.net/cod/cif/7/05/20/7052021.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_7052021
loop_
_publ_author_name
'Yuan, Ling'
'Sumpter, Bobby G.'
'Abboud, Khalil A.'
'Castellano, Ronald K.'
_publ_section_title
;
 Links between through-bond interactions and assembly structure in
 simple piperidones
;
_journal_issue                   11
_journal_name_full               'New Journal of Chemistry'
_journal_page_first              1924
_journal_paper_doi               10.1039/b808818g
_journal_volume                  32
_journal_year                    2008
_chemical_formula_sum            'C20 H23 N O'
_chemical_formula_weight         293.39
_chemical_name_systematic
;
?
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_audit_update_record
;
2008-02-04 # Formatted by publCIF
;
_cell_angle_alpha                90.00
_cell_angle_beta                 102.928(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   9.5059(7)
_cell_length_b                   12.3970(9)
_cell_length_c                   14.7096(11)
_cell_measurement_reflns_used    97
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      28.0
_cell_measurement_theta_min      2.0
_cell_volume                     1689.5(2)
_computing_cell_refinement
'Bruker SMART v5.624 & SAINT 6.36a (Bruker 1998)'
_computing_data_collection       'Bruker SMART v5.624 (Bruker 1998)'
_computing_data_reduction        'Bruker SHELXTL v6.12 (Bruker 2000)'
_computing_molecular_graphics    'Bruker SHELXTL v6.12'
_computing_publication_material  'Bruker SHELXTL v6.12'
_computing_structure_refinement  'Bruker SHELXTL v6.12'
_computing_structure_solution    'Bruker SHELXTL v6.12'
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 0.976
_diffrn_measured_fraction_theta_max 0.976
_diffrn_measurement_device_type  'SMART CCD area detector'
_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  0.0427
_diffrn_reflns_av_sigmaI/netI    0.0687
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            10768
_diffrn_reflns_theta_full        27.50
_diffrn_reflns_theta_max         27.50
_diffrn_reflns_theta_min         2.17
_diffrn_standards_decay_%        '< 1'
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.070
_exptl_absorpt_correction_T_max  0.9920
_exptl_absorpt_correction_T_min  0.9827
_exptl_absorpt_correction_type   integration
_exptl_absorpt_process_details
'based on measured indexed crystal faces, Bruker SHELXTL v6.12 (Bruker 1998)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.153
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needles
_exptl_crystal_F_000             632
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.23
_exptl_crystal_size_min          0.11
_refine_diff_density_max         0.114
_refine_diff_density_min         -0.142
_refine_diff_density_rms         0.029
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.787
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     199
_refine_ls_number_reflns         3786
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.787
_refine_ls_R_factor_all          0.0696
_refine_ls_R_factor_gt           0.0333
_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)+(0.0345P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0668
_refine_ls_wR_factor_ref         0.0708
_reflns_number_gt                2040
_reflns_number_total             3786
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            b808818g.txt
_cod_data_source_block           compound-2
_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_enum 1527 2010-12-29 10:47:43Z saulius 
;
_cod_original_sg_symbol_H-M      P21/n
_cod_database_code               7052021
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -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
_atom_site_disorder_assembly
_atom_site_disorder_group
N1 N 0.14590(9) 0.37669(7) 1.05257(6) 0.0332(2) Uani 1 1 d . . .
O1 O 0.37487(8) 0.64176(6) 1.03171(5) 0.0418(2) Uani 1 1 d . . .
C2 C 0.20325(12) 0.44657(9) 1.13223(7) 0.0354(3) Uani 1 1 d . . .
H2A H 0.3055 0.4279 1.1587 0.042 Uiso 1 1 calc R . .
H2B H 0.1483 0.4350 1.1812 0.042 Uiso 1 1 calc R . .
C3 C 0.19225(11) 0.56554(8) 1.10233(7) 0.0308(3) Uani 1 1 d . . .
H3A H 0.0884 0.5807 1.0739 0.037 Uiso 1 1 calc R . .
C4 C 0.27487(12) 0.57896(9) 1.02651(7) 0.0311(3) Uani 1 1 d . . .
C5 C 0.22713(12) 0.50328(9) 0.94505(7) 0.0310(3) Uani 1 1 d . . .
H5A H 0.1243 0.5205 0.9155 0.037 Uiso 1 1 calc R . .
C6 C 0.23208(12) 0.38773(9) 0.98242(8) 0.0353(3) Uani 1 1 d . . .
H6A H 0.1950 0.3376 0.9302 0.042 Uiso 1 1 calc R . .
H6B H 0.3334 0.3678 1.0103 0.042 Uiso 1 1 calc R . .
C7 C 0.14111(14) 0.26414(9) 1.08133(8) 0.0483(3) Uani 1 1 d . . .
H7A H 0.1023 0.2193 1.0266 0.072 Uiso 1 1 calc R . .
H7B H 0.0790 0.2578 1.1260 0.072 Uiso 1 1 calc R . .
H7C H 0.2388 0.2398 1.1107 0.072 Uiso 1 1 calc R . .
C8 C 0.31482(12) 0.51511(9) 0.87015(7) 0.0386(3) Uani 1 1 d . . .
H8A H 0.3275 0.5928 0.8586 0.046 Uiso 1 1 calc R . .
H8B H 0.4118 0.4836 0.8938 0.046 Uiso 1 1 calc R . .
C9 C 0.24581(12) 0.46133(9) 0.77911(8) 0.0347(3) Uani 1 1 d . . .
C10 C 0.12262(13) 0.50444(10) 0.72154(8) 0.0430(3) Uani 1 1 d . . .
H10A H 0.0805 0.5676 0.7406 0.052 Uiso 1 1 calc R . .
C11 C 0.05978(15) 0.45702(12) 0.63665(9) 0.0547(4) Uani 1 1 d . . .
H11A H -0.0247 0.4875 0.5985 0.066 Uiso 1 1 calc R . .
C12 C 0.11995(17) 0.36578(12) 0.60784(10) 0.0599(4) Uani 1 1 d . . .
H12A H 0.0770 0.3329 0.5499 0.072 Uiso 1 1 calc R . .
C13 C 0.24242(16) 0.32262(11) 0.66337(11) 0.0565(4) Uani 1 1 d . . .
H13A H 0.2852 0.2603 0.6433 0.068 Uiso 1 1 calc R . .
C14 C 0.30425(13) 0.36941(10) 0.74876(9) 0.0452(3) Uani 1 1 d . . .
H14A H 0.3880 0.3378 0.7870 0.054 Uiso 1 1 calc R . .
C15 C 0.23891(12) 0.64290(9) 1.18469(7) 0.0360(3) Uani 1 1 d . . .
H15A H 0.2141 0.6109 1.2407 0.043 Uiso 1 1 calc R . .
H15B H 0.3450 0.6520 1.1978 0.043 Uiso 1 1 calc R . .
C16 C 0.16815(12) 0.75202(9) 1.16655(7) 0.0319(3) Uani 1 1 d . . .
C17 C 0.03687(13) 0.77080(10) 1.19026(8) 0.0388(3) Uani 1 1 d . . .
H17A H -0.0050 0.7158 1.2206 0.047 Uiso 1 1 calc R . .
C18 C -0.03390(14) 0.86842(11) 1.17043(8) 0.0480(3) Uani 1 1 d . . .
H18A H -0.1238 0.8796 1.1870 0.058 Uiso 1 1 calc R . .
C19 C 0.02525(15) 0.94939(11) 1.12686(8) 0.0511(4) Uani 1 1 d . . .
H19A H -0.0234 1.0164 1.1133 0.061 Uiso 1 1 calc R . .
C20 C 0.15572(14) 0.93222(10) 1.10316(8) 0.0484(3) Uani 1 1 d . . .
H20A H 0.1973 0.9877 1.0731 0.058 Uiso 1 1 calc R . .
C21 C 0.22632(13) 0.83485(9) 1.12296(8) 0.0394(3) Uani 1 1 d . . .
H21A H 0.3164 0.8243 1.1065 0.047 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
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C6 N1 C2 110.09(9) . . ?
C6 N1 C7 110.65(9) . . ?
C2 N1 C7 111.35(8) . . ?
N1 C2 C3 110.51(9) . . ?
N1 C2 H2A 109.5 . . ?
C3 C2 H2A 109.5 . . ?
N1 C2 H2B 109.5 . . ?
C3 C2 H2B 109.5 . . ?
H2A C2 H2B 108.1 . . ?
C4 C3 C15 114.14(9) . . ?
C4 C3 C2 107.70(8) . . ?
C15 C3 C2 112.70(9) . . ?
C4 C3 H3A 107.3 . . ?
C15 C3 H3A 107.3 . . ?
C2 C3 H3A 107.3 . . ?
O1 C4 C5 122.62(10) . . ?
O1 C4 C3 123.48(10) . . ?
C5 C4 C3 113.84(9) . . ?
C4 C5 C8 113.36(9) . . ?
C4 C5 C6 108.47(9) . . ?
C8 C5 C6 111.73(9) . . ?
C4 C5 H5A 107.7 . . ?
C8 C5 H5A 107.7 . . ?
C6 C5 H5A 107.7 . . ?
N1 C6 C5 111.36(8) . . ?
N1 C6 H6A 109.4 . . ?
C5 C6 H6A 109.4 . . ?
N1 C6 H6B 109.4 . . ?
C5 C6 H6B 109.4 . . ?
H6A C6 H6B 108.0 . . ?
N1 C7 H7A 109.5 . . ?
N1 C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
N1 C7 H7C 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
C9 C8 C5 113.47(9) . . ?
C9 C8 H8A 108.9 . . ?
C5 C8 H8A 108.9 . . ?
C9 C8 H8B 108.9 . . ?
C5 C8 H8B 108.9 . . ?
H8A C8 H8B 107.7 . . ?
C14 C9 C10 117.66(11) . . ?
C14 C9 C8 121.59(11) . . ?
C10 C9 C8 120.73(11) . . ?
C11 C10 C9 121.31(12) . . ?
C11 C10 H10A 119.3 . . ?
C9 C10 H10A 119.3 . . ?
C12 C11 C10 120.00(13) . . ?
C12 C11 H11A 120.0 . . ?
C10 C11 H11A 120.0 . . ?
C13 C12 C11 119.52(13) . . ?
C13 C12 H12A 120.2 . . ?
C11 C12 H12A 120.2 . . ?
C12 C13 C14 120.43(13) . . ?
C12 C13 H13A 119.8 . . ?
C14 C13 H13A 119.8 . . ?
C9 C14 C13 121.07(13) . . ?
C9 C14 H14A 119.5 . . ?
C13 C14 H14A 119.5 . . ?
C16 C15 C3 112.53(9) . . ?
C16 C15 H15A 109.1 . . ?
C3 C15 H15A 109.1 . . ?
C16 C15 H15B 109.1 . . ?
C3 C15 H15B 109.1 . . ?
H15A C15 H15B 107.8 . . ?
C17 C16 C21 117.71(11) . . ?
C17 C16 C15 119.76(10) . . ?
C21 C16 C15 122.48(10) . . ?
C18 C17 C16 121.04(11) . . ?
C18 C17 H17A 119.5 . . ?
C16 C17 H17A 119.5 . . ?
C19 C18 C17 120.39(12) . . ?
C19 C18 H18A 119.8 . . ?
C17 C18 H18A 119.8 . . ?
C18 C19 C20 119.31(12) . . ?
C18 C19 H19A 120.3 . . ?
C20 C19 H19A 120.3 . . ?
C19 C20 C21 120.29(12) . . ?
C19 C20 H20A 119.9 . . ?
C21 C20 H20A 119.9 . . ?
C20 C21 C16 121.26(12) . . ?
C20 C21 H21A 119.4 . . ?
C16 C21 H21A 119.4 . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
N1 C6 1.4604(13) . ?
N1 C2 1.4611(13) . ?
N1 C7 1.4617(13) . ?
O1 C4 1.2178(12) . ?
C2 C3 1.5359(15) . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C3 C4 1.5100(14) . ?
C3 C15 1.5309(14) . ?
C3 H3A 1.0000 . ?
C4 C5 1.5096(15) . ?
C5 C8 1.5301(14) . ?
C5 C6 1.5312(14) . ?
C5 H5A 1.0000 . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C7 H7A 0.9800 . ?
C7 H7B 0.9800 . ?
C7 H7C 0.9800 . ?
C8 C9 1.5083(15) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C9 C14 1.3848(15) . ?
C9 C10 1.3893(16) . ?
C10 C11 1.3885(16) . ?
C10 H10A 0.9500 . ?
C11 C12 1.3764(18) . ?
C11 H11A 0.9500 . ?
C12 C13 1.3724(18) . ?
C12 H12A 0.9500 . ?
C13 C14 1.3889(17) . ?
C13 H13A 0.9500 . ?
C14 H14A 0.9500 . ?
C15 C16 1.5078(15) . ?
C15 H15A 0.9900 . ?
C15 H15B 0.9900 . ?
C16 C17 1.3884(15) . ?
C16 C21 1.3892(15) . ?
C17 C18 1.3835(16) . ?
C17 H17A 0.9500 . ?
C18 C19 1.3769(17) . ?
C18 H18A 0.9500 . ?
C19 C20 1.3779(17) . ?
C19 H19A 0.9500 . ?
C20 C21 1.3802(15) . ?
C20 H20A 0.9500 . ?
C21 H21A 0.9500 . ?
