#------------------------------------------------------------------------------
#$Date: 2017-10-13 14:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201982 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/02/20/4022080.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_4022080
loop_
_publ_author_name
'Paul R. Carlier'
'Yiqun Zhang'
'Carla Slebodnick'
'Michael M.-C. Lo'
'Ian D. Williams'
_publ_section_title
;
 Effect of 2,6-Disubstituted Aryl Groups on Acyclic Conformation:
 Preference for an Antiperiplanar Orientation of the Geminal
 and Vicinal Hydrogens
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              8835
_journal_page_last               8841
_journal_paper_doi               10.1021/jo061495z
_journal_volume                  71
_journal_year                    2006
_chemical_absolute_configuration unk
_chemical_formula_sum            'C16 H23 N O'
_chemical_formula_weight         245.35
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           4
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 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                 111.051(4)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   11.539(2)
_cell_length_b                   5.6179(11)
_cell_length_c                   11.803(2)
_cell_measurement_temperature    173(2)
_cell_volume                     714.1(2)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 0.983
_diffrn_measured_fraction_theta_max 0.983
_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  0.0786
_diffrn_reflns_av_sigmaI/netI    0.1212
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -4
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            3632
_diffrn_reflns_theta_full        25.25
_diffrn_reflns_theta_max         25.25
_diffrn_reflns_theta_min         1.85
_exptl_absorpt_coefficient_mu    0.070
_exptl_absorpt_correction_T_max  1.00
_exptl_absorpt_correction_T_min  0.78
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            Colorless
_exptl_crystal_density_diffrn    1.141
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Bar
_exptl_crystal_F_000             268
_exptl_crystal_size_max          0.7
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.06
_refine_diff_density_max         0.153
_refine_diff_density_min         -0.153
_refine_diff_density_rms         0.037
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.893
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     169
_refine_ls_number_reflns         1413
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      0.893
_refine_ls_R_factor_all          0.1059
_refine_ls_R_factor_gt           0.0517
_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)+(0.0050P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0590
_refine_ls_wR_factor_ref         0.0655
_reflns_number_gt                880
_reflns_number_total             1413
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo061495zsi20060718_110455.cif
_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      'P 21'
_cod_database_code               4022080
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, 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
C1 C 0.7823(3) 0.0194(7) 0.2056(3) 0.0234(9) Uani 1 1 d .
H1A H 0.8525 0.0648 0.2813 0.028 Uiso 1 1 calc R
O1 O 0.72187(19) 0.2347(4) 0.15812(19) 0.0282(6) Uani 1 1 d .
H1 H 0.6754 0.2174 0.0842 0.042 Uiso 1 1 d R
C3 C 0.5718(3) -0.1801(7) 0.1522(3) 0.0289(10) Uani 1 1 d .
N3 N 0.4775(3) -0.2161(6) 0.0794(3) 0.0378(9) Uani 1 1 d .
C2 C 0.6962(3) -0.1457(7) 0.2489(3) 0.0237(9) Uani 1 1 d .
H2A H 0.7368 -0.3058 0.2649 0.028 Uiso 1 1 calc R
C10 C 0.8446(3) -0.1025(6) 0.1230(3) 0.0239(9) Uani 1 1 d .
C11 C 0.7494(3) -0.2113(7) 0.0082(3) 0.0337(10) Uani 1 1 d .
H11A H 0.7923 -0.2751 -0.0434 0.051 Uiso 1 1 calc R
H11B H 0.6904 -0.0883 -0.0364 0.051 Uiso 1 1 calc R
H11C H 0.7046 -0.3399 0.0309 0.051 Uiso 1 1 calc R
C12 C 0.9210(3) 0.0899(7) 0.0877(3) 0.0347(10) Uani 1 1 d .
H12A H 0.9701 0.0154 0.0447 0.052 Uiso 1 1 calc R
H12B H 0.9767 0.1685 0.1612 0.052 Uiso 1 1 calc R
H12C H 0.8647 0.2079 0.0348 0.052 Uiso 1 1 calc R
C13 C 0.9336(3) -0.2960(7) 0.1953(3) 0.0346(10) Uani 1 1 d .
H13A H 0.8858 -0.4306 0.2083 0.052 Uiso 1 1 calc R
H13B H 0.9868 -0.2316 0.2740 0.052 Uiso 1 1 calc R
H13C H 0.9852 -0.3499 0.1501 0.052 Uiso 1 1 calc R
C21 C 0.6893(3) -0.0585(7) 0.3712(3) 0.0258(9) Uani 1 1 d .
C22 C 0.7745(3) -0.1632(7) 0.4779(3) 0.0306(10) Uani 1 1 d .
C23 C 0.7803(3) -0.0714(8) 0.5909(3) 0.0372(11) Uani 1 1 d .
H23A H 0.8378 -0.1393 0.6629 0.045 Uiso 1 1 calc R
C24 C 0.7055(3) 0.1144(8) 0.6010(3) 0.0361(11) Uani 1 1 d .
C25 C 0.6222(3) 0.2061(7) 0.4958(3) 0.0358(10) Uani 1 1 d .
H25A H 0.5692 0.3310 0.5018 0.043 Uiso 1 1 calc R
C26 C 0.6107(3) 0.1255(7) 0.3792(3) 0.0290(10) Uani 1 1 d .
C27 C 0.8609(3) -0.3642(7) 0.4772(3) 0.0432(12) Uani 1 1 d .
H27A H 0.9201 -0.3092 0.4406 0.065 Uiso 1 1 calc R
H27B H 0.8126 -0.4975 0.4298 0.065 Uiso 1 1 calc R
H27C H 0.9062 -0.4165 0.5607 0.065 Uiso 1 1 calc R
C28 C 0.7199(3) 0.2210(8) 0.7244(3) 0.0514(13) Uani 1 1 d .
H28A H 0.7659 0.1098 0.7888 0.077 Uiso 1 1 calc R
H28B H 0.6376 0.2499 0.7282 0.077 Uiso 1 1 calc R
H28C H 0.7655 0.3716 0.7352 0.077 Uiso 1 1 calc R
C29 C 0.5135(3) 0.2455(8) 0.2728(3) 0.0415(11) Uani 1 1 d .
H29A H 0.5455 0.2658 0.2069 0.062 Uiso 1 1 calc R
H29B H 0.4935 0.4016 0.2980 0.062 Uiso 1 1 calc R
H29C H 0.4384 0.1469 0.2445 0.062 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
O1 C1 C10 113.7(3)
O1 C1 C2 110.9(3)
C10 C1 C2 115.5(3)
N3 C3 C2 177.2(4)
C3 C2 C21 113.3(3)
C3 C2 C1 112.0(3)
C21 C2 C1 111.4(3)
C13 C10 C11 109.6(3)
C13 C10 C12 108.3(3)
C11 C10 C12 109.8(3)
C13 C10 C1 109.3(3)
C11 C10 C1 112.5(3)
C12 C10 C1 107.3(3)
C26 C21 C22 120.3(3)
C26 C21 C2 123.1(3)
C22 C21 C2 116.4(3)
C23 C22 C21 118.1(3)
C23 C22 C27 118.2(3)
C21 C22 C27 123.7(3)
C24 C23 C22 122.5(4)
C25 C24 C23 117.5(4)
C25 C24 C28 121.2(4)
C23 C24 C28 121.3(3)
C24 C25 C26 123.7(4)
C21 C26 C25 117.8(3)
C21 C26 C29 125.4(3)
C25 C26 C29 116.8(3)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C1 O1 1.408(4)
C1 C10 1.563(4)
C1 C2 1.572(4)
C3 N3 1.136(4)
C3 C2 1.492(4)
C2 C21 1.554(4)
C10 C13 1.528(4)
C10 C11 1.532(4)
C10 C12 1.544(4)
C21 C26 1.401(4)
C21 C22 1.418(4)
C22 C23 1.408(4)
C22 C27 1.508(5)
C23 C24 1.387(5)
C24 C25 1.369(4)
C24 C28 1.527(4)
C25 C26 1.409(4)
C26 C29 1.509(4)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 10163886
