#------------------------------------------------------------------------------
#$Date: 2022-09-14 21:32:59 +0300 (Wed, 14 Sep 2022) $
#$Revision: 277840 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/02/20/4022072.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_4022072
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_moiety         'C22 H21 N O'
_chemical_formula_sum            'C22 H21 N O'
_chemical_formula_weight         315.40
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           61
_space_group_name_Hall           '-P 2ac 2ab'
_space_group_name_H-M_alt        'P b c a'
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  '-P 2ac 2ab'
_symmetry_space_group_name_H-M   'P b c a'
_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                   7.5969(3)
_cell_length_b                   19.9937(8)
_cell_length_c                   22.450(7)
_cell_measurement_reflns_used    4189
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      25.03
_cell_measurement_theta_min      4.14
_cell_volume                     3409.9(11)
_computing_cell_refinement       'CrysAlis (Oxford Diffraction)'
_computing_data_collection       'CrysAlis (Oxford Diffraction)'
_computing_data_reduction        'CrysAlis (Oxford Diffraction)'
_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      100(2)
_diffrn_detector                 CCD
_diffrn_detector_type            'Oxford Diffraction Sapphire 3 CCD'
_diffrn_measured_fraction_theta_full 0.984
_diffrn_measured_fraction_theta_max 0.984
_diffrn_measurement_device       'κ-geometry diffractometer'
_diffrn_measurement_device_type  'Oxford Diffraction Xcalibur'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0738
_diffrn_reflns_av_sigmaI/netI    0.0833
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            14891
_diffrn_reflns_theta_full        25.11
_diffrn_reflns_theta_max         25.11
_diffrn_reflns_theta_min         3.83
_diffrn_source                   'fine-focus sealed tube'
_diffrn_source_current           40
_diffrn_source_voltage           50
_diffrn_standards_decay_%        <2%
_diffrn_standards_interval_count 50
_diffrn_standards_number         2
_exptl_absorpt_coefficient_mu    0.075
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.229
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             1344
_exptl_crystal_size_max          0.23
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.03
_refine_diff_density_max         0.160
_refine_diff_density_min         -0.142
_refine_diff_density_rms         0.034
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.842
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     224
_refine_ls_number_reflns         2981
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.842
_refine_ls_R_factor_all          0.0950
_refine_ls_R_factor_gt           0.0360
_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)+(0.0316P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0623
_refine_ls_wR_factor_ref         0.0720
_reflns_number_gt                1653
_reflns_number_total             2981
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo061495zsi20060718_110121.cif
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Orthorhombic' changed to 'orthorhombic'
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_database_code               4022072
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'x, -y-1/2, 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
O1 O -0.18104(18) 0.24167(6) 0.63907(5) 0.0237(3) Uani 1 1 d .
N1 N 0.0582(2) 0.26228(8) 0.77024(8) 0.0354(5) Uani 1 1 d .
C1 C -0.0784(2) 0.32148(9) 0.56515(7) 0.0185(4) Uani 1 1 d .
C2 C -0.0308(2) 0.27316(8) 0.52212(7) 0.0182(4) Uani 1 1 d .
C3 C -0.0099(2) 0.29351(9) 0.46333(7) 0.0211(4) Uani 1 1 d .
H3 H 0.0244 0.2612 0.4346 0.025 Uiso 1 1 calc R
C4 C -0.0367(2) 0.35888(9) 0.44484(8) 0.0210(4) Uani 1 1 d .
C5 C -0.0883(2) 0.40508(9) 0.48758(7) 0.0208(4) Uani 1 1 d .
H5 H -0.1112 0.4499 0.4758 0.025 Uiso 1 1 calc R
C6 C -0.1075(2) 0.38766(9) 0.54731(7) 0.0201(4) Uani 1 1 d .
C7 C -0.0017(2) 0.20028(8) 0.53580(7) 0.0226(4) Uani 1 1 d .
H7A H -0.1154 0.1784 0.5423 0.034 Uiso 1 1 calc R
H7B H 0.0706 0.1961 0.5718 0.034 Uiso 1 1 calc R
H7C H 0.0589 0.1790 0.5023 0.034 Uiso 1 1 calc R
C8 C -0.0069(3) 0.37873(9) 0.38116(7) 0.0273(5) Uani 1 1 d .
H8A H 0.1194 0.3849 0.3742 0.041 Uiso 1 1 calc R
H8B H -0.0691 0.4207 0.3729 0.041 Uiso 1 1 calc R
H8C H -0.0517 0.3436 0.3548 0.041 Uiso 1 1 calc R
C9 C -0.1551(2) 0.44265(9) 0.59077(7) 0.0249(5) Uani 1 1 d .
H9A H -0.0538 0.4522 0.6165 0.037 Uiso 1 1 calc R
H9B H -0.2549 0.4283 0.6153 0.037 Uiso 1 1 calc R
H9C H -0.1873 0.4831 0.5687 0.037 Uiso 1 1 calc R
C10 C -0.0897(2) 0.30333(9) 0.63056(7) 0.0204(4) Uani 1 1 d .
H10 H -0.1561 0.3394 0.6517 0.025 Uiso 1 1 calc R
C11 C 0.0997(2) 0.29795(9) 0.65921(7) 0.0208(4) Uani 1 1 d .
H11 H 0.1658 0.2621 0.6376 0.025 Uiso 1 1 calc R
C12 C 0.0786(2) 0.27674(9) 0.72143(9) 0.0257(5) Uani 1 1 d .
C13 C 0.2051(2) 0.36258(9) 0.65442(8) 0.0209(4) Uani 1 1 d .
C14 C 0.2080(2) 0.40879(9) 0.69912(8) 0.0232(5) Uani 1 1 d .
H14 H 0.1509 0.3992 0.7358 0.028 Uiso 1 1 calc R
C15 C 0.2958(2) 0.47158(9) 0.69160(7) 0.0202(4) Uani 1 1 d .
C16 C 0.2978(2) 0.52010(9) 0.73703(8) 0.0261(5) Uani 1 1 d .
H16 H 0.2428 0.5109 0.7742 0.031 Uiso 1 1 calc R
C17 C 0.3786(3) 0.58044(10) 0.72788(8) 0.0280(5) Uani 1 1 d .
H17 H 0.3784 0.6130 0.7587 0.034 Uiso 1 1 calc R
C18 C 0.4621(2) 0.59484(10) 0.67334(8) 0.0279(5) Uani 1 1 d .
H18 H 0.5187 0.6368 0.6678 0.033 Uiso 1 1 calc R
C19 C 0.4621(2) 0.54896(9) 0.62856(8) 0.0262(5) Uani 1 1 d .
H19 H 0.5179 0.5592 0.5918 0.031 Uiso 1 1 calc R
C20 C 0.3788(2) 0.48556(9) 0.63640(8) 0.0223(4) Uani 1 1 d .
C21 C 0.3756(2) 0.43643(9) 0.59132(8) 0.0259(5) Uani 1 1 d .
H21 H 0.4317 0.4451 0.5543 0.031 Uiso 1 1 calc R
C22 C 0.2930(2) 0.37650(9) 0.60018(8) 0.0243(5) Uani 1 1 d .
H22 H 0.2946 0.3437 0.5695 0.029 Uiso 1 1 calc R
H1 H -0.267(3) 0.2459(11) 0.6656(10) 0.065(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
C6 C1 C2 119.41(15)
C6 C1 C10 119.64(15)
C2 C1 C10 120.89(16)
C3 C2 C1 118.57(16)
C3 C2 C7 117.38(15)
C1 C2 C7 124.05(15)
C4 C3 C2 122.90(16)
C3 C4 C5 117.51(16)
C3 C4 C8 120.82(16)
C5 C4 C8 121.66(16)
C4 C5 C6 121.90(17)
C5 C6 C1 119.67(15)
C5 C6 C9 117.63(16)
C1 C6 C9 122.68(15)
O1 C10 C1 111.35(13)
O1 C10 C11 109.24(13)
C1 C10 C11 111.04(13)
C12 C11 C13 111.68(14)
C12 C11 C10 107.89(14)
C13 C11 C10 113.08(14)
N1 C12 C11 177.4(2)
C14 C13 C22 119.44(16)
C14 C13 C11 122.07(16)
C22 C13 C11 118.36(15)
C13 C14 C15 120.97(16)
C16 C15 C20 119.52(17)
C16 C15 C14 121.57(17)
C20 C15 C14 118.89(16)
C17 C16 C15 120.21(17)
C16 C17 C18 120.83(17)
C19 C18 C17 120.27(18)
C18 C19 C20 120.50(17)
C21 C20 C15 118.83(17)
C21 C20 C19 122.50(17)
C15 C20 C19 118.67(16)
C22 C21 C20 120.91(17)
C21 C22 C13 120.92(17)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O1 C10 1.428(2)
N1 C12 1.144(2)
C1 C6 1.400(2)
C1 C2 1.413(2)
C1 C10 1.515(2)
C2 C3 1.390(2)
C2 C7 1.506(2)
C3 C4 1.386(2)
C4 C5 1.388(2)
C4 C8 1.501(2)
C5 C6 1.393(2)
C6 C9 1.514(2)
C10 C11 1.580(2)
C11 C12 1.469(3)
C11 C13 1.524(2)
C13 C14 1.364(2)
C13 C22 1.416(2)
C14 C15 1.432(2)
C15 C16 1.408(2)
C15 C20 1.418(2)
C16 C17 1.369(2)
C17 C18 1.409(2)
C18 C19 1.361(2)
C19 C20 1.428(2)
C20 C21 1.411(2)
C21 C22 1.367(2)
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
_geom_hbond_site_symmetry_A
O1 H1 N1 0.89(2) 1.99(2) 2.870(2) 174(2) 6_557
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
C6 C1 C2 C3 1.7(2)
C10 C1 C2 C3 -175.38(15)
C6 C1 C2 C7 -178.07(16)
C10 C1 C2 C7 4.8(3)
C1 C2 C3 C4 -1.2(3)
C7 C2 C3 C4 178.57(16)
C2 C3 C4 C5 -0.6(3)
C2 C3 C4 C8 178.11(17)
C3 C4 C5 C6 2.0(3)
C8 C4 C5 C6 -176.70(17)
C4 C5 C6 C1 -1.5(3)
C4 C5 C6 C9 176.86(16)
C2 C1 C6 C5 -0.4(2)
C10 C1 C6 C5 176.74(16)
C2 C1 C6 C9 -178.69(16)
C10 C1 C6 C9 -1.6(2)
C6 C1 C10 O1 137.57(16)
C2 C1 C10 O1 -45.3(2)
C6 C1 C10 C11 -100.46(18)
C2 C1 C10 C11 76.63(19)
O1 C10 C11 C12 -53.78(18)
C1 C10 C11 C12 -176.97(14)
O1 C10 C11 C13 -177.80(14)
C1 C10 C11 C13 59.01(18)
C12 C11 C13 C14 -27.5(2)
C10 C11 C13 C14 94.42(19)
C12 C11 C13 C22 156.60(16)
C10 C11 C13 C22 -81.5(2)
C22 C13 C14 C15 1.2(3)
C11 C13 C14 C15 -174.69(16)
C13 C14 C15 C16 179.08(17)
C13 C14 C15 C20 0.7(2)
C20 C15 C16 C17 0.2(3)
C14 C15 C16 C17 -178.14(17)
C15 C16 C17 C18 -0.5(3)
C16 C17 C18 C19 0.6(3)
C17 C18 C19 C20 -0.5(3)
C16 C15 C20 C21 -179.99(16)
C14 C15 C20 C21 -1.6(2)
C16 C15 C20 C19 -0.1(2)
C14 C15 C20 C19 178.34(16)
C18 C19 C20 C21 -179.88(17)
C18 C19 C20 C15 0.2(3)
C15 C20 C21 C22 0.6(3)
C19 C20 C21 C22 -179.33(18)
C20 C21 C22 C13 1.3(3)
C14 C13 C22 C21 -2.2(3)
C11 C13 C22 C21 173.81(17)
