#------------------------------------------------------------------------------
#$Date: 2016-03-21 02:36:20 +0200 (Mon, 21 Mar 2016) $
#$Revision: 178398 $
#$URL: svn://www.crystallography.net/cod/cif/4/02/20/4022082.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_4022082
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_formula_sum            'C19 H21 N O2'
_chemical_formula_weight         295.37
_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
_cell_angle_alpha                90.00
_cell_angle_beta                 96.720(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   11.637(2)
_cell_length_b                   8.2270(10)
_cell_length_c                   17.298(4)
_cell_measurement_temperature    203(2)
_cell_volume                     1644.7(5)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      203(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  0.0249
_diffrn_reflns_av_sigmaI/netI    0.0581
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            3705
_diffrn_reflns_theta_full        27.00
_diffrn_reflns_theta_max         27.00
_diffrn_reflns_theta_min         2.01
_exptl_absorpt_coefficient_mu    0.077
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            Colorless
_exptl_crystal_density_diffrn    1.193
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Prism
_exptl_crystal_F_000             632
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.4
_exptl_crystal_size_min          0.3
_refine_diff_density_max         0.202
_refine_diff_density_min         -0.197
_refine_diff_density_rms         0.038
_refine_ls_extinction_coef       0.0081(15)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   0.971
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     204
_refine_ls_number_reflns         3532
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.971
_refine_ls_R_factor_all          0.0995
_refine_ls_R_factor_gt           0.0497
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0400P)²+0.3800P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0984
_refine_ls_wR_factor_ref         0.1120
_reflns_number_gt                2197
_reflns_number_total             3532
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo061495zsi20060718_110549.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.

'_exptl_absorpt_correction_type' value 'None' changed to
'none' 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/n'
_cod_database_code               4022082
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
O1 O 0.51883(10) 0.29644(15) 0.14663(7) 0.0335(3) Uani 1 1 d .
C1 C 0.46062(15) 0.4516(2) 0.14307(10) 0.0283(4) Uani 1 1 d .
H1A H 0.4542 0.4902 0.0885 0.034 Uiso 1 1 calc R
C2 C 0.33690(15) 0.4209(2) 0.16399(9) 0.0276(4) Uani 1 1 d .
H2A H 0.2992 0.5280 0.1677 0.033 Uiso 1 1 calc R
C3 C 0.33610(15) 0.3396(2) 0.23915(11) 0.0349(4) Uani 1 1 d .
N3 N 0.33049(15) 0.2738(2) 0.29651(9) 0.0508(5) Uani 1 1 d .
O4 O 0.51852(14) 0.28789(18) 0.01686(8) 0.0519(4) Uani 1 1 d .
C4 C 0.54384(16) 0.2289(2) 0.07954(11) 0.0363(4) Uani 1 1 d .
C5 C 0.6069(2) 0.0726(3) 0.09446(15) 0.0557(6) Uani 1 1 d .
H5A H 0.6683 0.0653 0.0612 0.083 Uiso 1 1 calc R
H5B H 0.5536 -0.0173 0.0834 0.083 Uiso 1 1 calc R
H5C H 0.6400 0.0680 0.1485 0.083 Uiso 1 1 calc R
C11 C 0.53544(16) 0.5741(2) 0.19365(10) 0.0342(4) Uani 1 1 d .
C12 C 0.56603(19) 0.5183(3) 0.27785(11) 0.0530(6) Uani 1 1 d .
H12A H 0.6226 0.5919 0.3044 0.080 Uiso 1 1 calc R
H12B H 0.5980 0.4093 0.2784 0.080 Uiso 1 1 calc R
H12C H 0.4968 0.5181 0.3041 0.080 Uiso 1 1 calc R
C13 C 0.64745(18) 0.5969(3) 0.15671(12) 0.0507(6) Uani 1 1 d .
H13A H 0.6953 0.6778 0.1858 0.076 Uiso 1 1 calc R
H13B H 0.6292 0.6327 0.1033 0.076 Uiso 1 1 calc R
H13C H 0.6889 0.4945 0.1577 0.076 Uiso 1 1 calc R
C14 C 0.47209(19) 0.7358(3) 0.19260(13) 0.0482(5) Uani 1 1 d .
H14A H 0.5242 0.8189 0.2160 0.072 Uiso 1 1 calc R
H14B H 0.4063 0.7261 0.2219 0.072 Uiso 1 1 calc R
H14C H 0.4454 0.7656 0.1393 0.072 Uiso 1 1 calc R
C21 C 0.26336(14) 0.3227(2) 0.10154(10) 0.0283(4) Uani 1 1 d .
C22 C 0.25115(17) 0.1582(2) 0.10972(11) 0.0372(5) Uani 1 1 d .
H22A H 0.2900 0.1059 0.1535 0.045 Uiso 1 1 calc R
C23 C 0.18180(18) 0.0663(3) 0.05405(12) 0.0434(5) Uani 1 1 d .
H23A H 0.1747 -0.0465 0.0607 0.052 Uiso 1 1 calc R
C24 C 0.12525(17) 0.1400(3) -0.00914(11) 0.0404(5) Uani 1 1 d .
H24A H 0.0790 0.0775 -0.0461 0.049 Uiso 1 1 calc R
C25 C 0.13436(15) 0.3091(2) -0.02057(10) 0.0325(4) Uani 1 1 d .
C26 C 0.07121(16) 0.3868(3) -0.08431(11) 0.0395(5) Uani 1 1 d .
H26A H 0.0236 0.3248 -0.1208 0.047 Uiso 1 1 calc R
C27 C 0.07806(17) 0.5501(3) -0.09387(11) 0.0420(5) Uani 1 1 d .
H27A H 0.0347 0.6006 -0.1365 0.050 Uiso 1 1 calc R
C28 C 0.14940(17) 0.6428(3) -0.04057(11) 0.0385(5) Uani 1 1 d .
H28A H 0.1543 0.7557 -0.0479 0.046 Uiso 1 1 calc R
C29 C 0.21222(15) 0.5723(2) 0.02207(10) 0.0327(4) Uani 1 1 d .
H29A H 0.2603 0.6370 0.0571 0.039 Uiso 1 1 calc R
C30 C 0.20582(14) 0.4031(2) 0.03487(10) 0.0291(4) Uani 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
C4 O1 C1 118.37(14)
O1 C1 C11 108.91(14)
O1 C1 C2 106.91(14)
C11 C1 C2 117.08(14)
C3 C2 C21 108.98(15)
C3 C2 C1 112.69(14)
C21 C2 C1 112.39(14)
N3 C3 C2 176.85(19)
O4 C4 O1 124.01(18)
O4 C4 C5 124.98(19)
O1 C4 C5 111.01(18)
C14 C11 C12 109.45(17)
C14 C11 C13 108.90(17)
C12 C11 C13 108.67(17)
C14 C11 C1 109.00(15)
C12 C11 C1 113.48(16)
C13 C11 C1 107.23(15)
C22 C21 C30 119.81(17)
C22 C21 C2 120.37(16)
C30 C21 C2 119.82(16)
C21 C22 C23 121.32(19)
C24 C23 C22 119.99(19)
C23 C24 C25 121.21(18)
C26 C25 C24 121.17(18)
C26 C25 C30 119.49(18)
C24 C25 C30 119.30(17)
C27 C26 C25 120.88(19)
C26 C27 C28 120.03(19)
C29 C28 C27 121.0(2)
C28 C29 C30 120.70(18)
C29 C30 C25 117.88(17)
C29 C30 C21 123.73(16)
C25 C30 C21 118.34(17)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O1 C4 1.349(2)
O1 C1 1.443(2)
C1 C11 1.537(2)
C1 C2 1.546(2)
C2 C3 1.463(2)
C2 C21 1.528(2)
C3 N3 1.139(2)
O4 C4 1.193(2)
C4 C5 1.488(3)
C11 C14 1.520(3)
C11 C12 1.529(3)
C11 C13 1.529(3)
C21 C22 1.369(3)
C21 C30 1.427(2)
C22 C23 1.403(3)
C23 C24 1.352(3)
C24 C25 1.410(3)
C25 C26 1.405(3)
C25 C30 1.422(2)
C26 C27 1.357(3)
C27 C28 1.394(3)
C28 C29 1.364(3)
C29 C30 1.413(3)
