#------------------------------------------------------------------------------
#$Date: 2022-09-14 21:32:59 +0300 (Wed, 14 Sep 2022) $
#$Revision: 277840 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/02/20/4022074.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_4022074
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         'C19 H13 Cl2 N O'
_chemical_formula_sum            'C19 H13 Cl2 N O'
_chemical_formula_weight         342.20
_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                   19.541(3)
_cell_length_b                   8.2533(9)
_cell_length_c                   20.397(3)
_cell_measurement_reflns_used    3008
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      20.90
_cell_measurement_theta_min      2.19
_cell_volume                     3289.6(7)
_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 0.995
_diffrn_measured_fraction_theta_max 0.995
_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  0.0277
_diffrn_reflns_av_sigmaI/netI    0.0170
_diffrn_reflns_limit_h_max       23
_diffrn_reflns_limit_h_min       -23
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            14692
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         4.41
_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    0.398
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.382
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             1408
_exptl_crystal_size_max          0.47
_exptl_crystal_size_mid          0.45
_exptl_crystal_size_min          0.38
_refine_diff_density_max         0.563
_refine_diff_density_min         -0.333
_refine_diff_density_rms         0.060
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.178
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     208
_refine_ls_number_reflns         2881
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.178
_refine_ls_R_factor_all          0.0580
_refine_ls_R_factor_gt           0.0550
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0658P)²+3.1177P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1366
_refine_ls_wR_factor_ref         0.1392
_reflns_number_gt                2758
_reflns_number_total             2881
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo061495zsi20060718_110206.cif
_cod_database_code               4022074
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
Cl1 Cl 0.10850(4) 0.65730(8) 0.45317(3) 0.0373(2) Uani 1 1 d .
Cl2 Cl 0.01082(4) 0.39583(8) 0.22563(3) 0.0410(2) Uani 1 1 d .
O1 O 0.13225(9) 0.6053(2) 0.24967(8) 0.0330(4) Uani 1 1 d .
H1 H 0.1470 0.7005 0.2533 0.050 Uiso 1 1 calc R
N1 N 0.28558(14) 0.3877(4) 0.26880(12) 0.0516(7) Uani 1 1 d .
C1 C 0.04257(13) 0.5918(3) 0.40211(13) 0.0299(6) Uani 1 1 d .
C2 C -0.02302(14) 0.6014(3) 0.42715(15) 0.0394(7) Uani 1 1 d .
H2 H -0.0306 0.6435 0.4699 0.047 Uiso 1 1 calc R
C3 C -0.07713(15) 0.5495(4) 0.38981(16) 0.0455(8) Uani 1 1 d .
H3 H -0.1224 0.5562 0.4066 0.055 Uiso 1 1 calc R
C4 C -0.06578(14) 0.4874(3) 0.32765(16) 0.0422(7) Uani 1 1 d .
H4 H -0.1032 0.4512 0.3017 0.051 Uiso 1 1 calc R
C5 C 0.00030(14) 0.4783(3) 0.30347(14) 0.0332(6) Uani 1 1 d .
C6 C 0.05680(12) 0.5320(3) 0.33947(12) 0.0260(5) Uani 1 1 d .
C7 C 0.12918(12) 0.5321(3) 0.31256(12) 0.0261(5) Uani 1 1 d .
H7 H 0.1588 0.5959 0.3431 0.031 Uiso 1 1 calc R
C8 C 0.15902(13) 0.3582(3) 0.30699(12) 0.0291(6) Uani 1 1 d .
H8 H 0.1325 0.2977 0.2730 0.035 Uiso 1 1 calc R
C9 C 0.23027(15) 0.3740(3) 0.28455(13) 0.0371(7) Uani 1 1 d .
C10 C 0.15400(13) 0.2667(3) 0.37132(13) 0.0315(6) Uani 1 1 d .
C11 C 0.19887(13) 0.2885(3) 0.42086(13) 0.0328(6) Uani 1 1 d .
H11 H 0.2372 0.3574 0.4143 0.039 Uiso 1 1 calc R
C12 C 0.19008(13) 0.2103(3) 0.48303(13) 0.0324(6) Uani 1 1 d .
C13 C 0.23536(15) 0.2358(4) 0.53495(13) 0.0404(7) Uani 1 1 d .
H13 H 0.2740 0.3041 0.5291 0.049 Uiso 1 1 calc R
C14 C 0.22440(17) 0.1632(4) 0.59403(15) 0.0462(7) Uani 1 1 d .
H14 H 0.2556 0.1817 0.6290 0.055 Uiso 1 1 calc R
C15 C 0.16761(17) 0.0612(4) 0.60413(14) 0.0465(8) Uani 1 1 d .
H15 H 0.1603 0.0125 0.6457 0.056 Uiso 1 1 calc R
C16 C 0.12307(16) 0.0326(4) 0.55387(15) 0.0428(7) Uani 1 1 d .
H16 H 0.0853 -0.0379 0.5605 0.051 Uiso 1 1 calc R
C17 C 0.13275(13) 0.1077(3) 0.49112(13) 0.0321(6) Uani 1 1 d .
C18 C 0.08742(14) 0.0834(3) 0.43824(15) 0.0392(7) Uani 1 1 d .
H18 H 0.0495 0.0125 0.4433 0.047 Uiso 1 1 calc R
C19 C 0.09745(14) 0.1602(3) 0.38008(15) 0.0370(6) Uani 1 1 d .
H19 H 0.0664 0.1427 0.3449 0.044 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'
Cl Cl 0.1484 0.1585 '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
C2 C1 C6 122.9(2)
C2 C1 Cl1 116.6(2)
C6 C1 Cl1 120.58(19)
C3 C2 C1 119.5(3)
C2 C3 C4 120.0(3)
C5 C4 C3 119.7(3)
C4 C5 C6 122.2(3)
C4 C5 Cl2 117.2(2)
C6 C5 Cl2 120.7(2)
C1 C6 C5 115.8(2)
C1 C6 C7 121.1(2)
C5 C6 C7 123.1(2)
O1 C7 C6 111.51(19)
O1 C7 C8 108.13(19)
C6 C7 C8 112.1(2)
C9 C8 C10 112.0(2)
C9 C8 C7 107.2(2)
C10 C8 C7 111.87(19)
N1 C9 C8 178.2(3)
C11 C10 C19 119.5(3)
C11 C10 C8 122.6(2)
C19 C10 C8 117.8(2)
C10 C11 C12 121.6(3)
C13 C12 C17 120.3(3)
C13 C12 C11 121.8(3)
C17 C12 C11 117.9(2)
C14 C13 C12 120.3(3)
C13 C14 C15 121.1(3)
C16 C15 C14 119.7(3)
C15 C16 C17 120.7(3)
C18 C17 C12 119.6(3)
C18 C17 C16 122.5(3)
C12 C17 C16 117.9(3)
C19 C18 C17 120.7(3)
C18 C19 C10 120.6(3)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
Cl1 C1 1.743(3)
Cl2 C5 1.740(3)
O1 C7 1.419(3)
N1 C9 1.133(4)
C1 C2 1.382(4)
C1 C6 1.398(4)
C2 C3 1.372(4)
C3 C4 1.386(5)
C4 C5 1.384(4)
C5 C6 1.398(4)
C6 C7 1.517(3)
C7 C8 1.553(3)
C8 C9 1.471(4)
C8 C10 1.517(4)
C10 C11 1.350(4)
C10 C19 1.423(4)
C11 C12 1.433(4)
C12 C13 1.396(4)
C12 C17 1.414(4)
C13 C14 1.363(4)
C14 C15 1.408(5)
C15 C16 1.365(4)
C16 C17 1.435(4)
C17 C18 1.410(4)
C18 C19 1.360(4)
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 0.84 2.06 2.857(3) 159.4 8_665
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 0.4(4)
Cl1 C1 C2 C3 -179.1(2)
C1 C2 C3 C4 0.3(4)
C2 C3 C4 C5 -0.1(4)
C3 C4 C5 C6 -0.9(4)
C3 C4 C5 Cl2 179.0(2)
C2 C1 C6 C5 -1.4(4)
Cl1 C1 C6 C5 178.13(18)
C2 C1 C6 C7 176.7(2)
Cl1 C1 C6 C7 -3.8(3)
C4 C5 C6 C1 1.6(4)
Cl2 C5 C6 C1 -178.26(18)
C4 C5 C6 C7 -176.4(2)
Cl2 C5 C6 C7 3.8(3)
C1 C6 C7 O1 -128.4(2)
C5 C6 C7 O1 49.4(3)
C1 C6 C7 C8 110.2(2)
C5 C6 C7 C8 -72.0(3)
O1 C7 C8 C9 60.2(2)
C6 C7 C8 C9 -176.5(2)
O1 C7 C8 C10 -176.7(2)
C6 C7 C8 C10 -53.3(3)
C9 C8 C10 C11 40.4(3)
C7 C8 C10 C11 -80.1(3)
C9 C8 C10 C19 -142.8(2)
C7 C8 C10 C19 96.7(3)
C19 C10 C11 C12 -1.7(4)
C8 C10 C11 C12 175.0(2)
C10 C11 C12 C13 -178.3(2)
C10 C11 C12 C17 0.4(4)
C17 C12 C13 C14 -0.6(4)
C11 C12 C13 C14 178.1(3)
C12 C13 C14 C15 0.1(4)
C13 C14 C15 C16 0.8(4)
C14 C15 C16 C17 -1.2(4)
C13 C12 C17 C18 179.9(2)
C11 C12 C17 C18 1.2(4)
C13 C12 C17 C16 0.2(4)
C11 C12 C17 C16 -178.5(2)
C15 C16 C17 C18 -179.0(3)
C15 C16 C17 C12 0.7(4)
C12 C17 C18 C19 -1.5(4)
C16 C17 C18 C19 178.3(3)
C17 C18 C19 C10 0.1(4)
C11 C10 C19 C18 1.5(4)
C8 C10 C19 C18 -175.4(2)
