#------------------------------------------------------------------------------
#$Date: 2017-10-14 22:27:35 +0300 (Sat, 14 Oct 2017) $
#$Revision: 202017 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/15/18/7151873.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_7151873
loop_
_publ_author_name
'Nagaraj, Muthupandi'
'Boominathan, Muthusamy'
'Muthusubramanian, Shanmugam'
'Bhuvanesh, Nattamai'
_publ_section_title
;
 Synthesis of novel N-hydroxy heterocycles via intramolecular reductive
 cyclization of diketoximes by NaBH3CN
;
_journal_issue                   12
_journal_name_full               'Organic & Biomolecular Chemistry'
_journal_page_first              4642
_journal_paper_doi               10.1039/c1ob05232b
_journal_volume                  9
_journal_year                    2011
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C21 H24 Cl N O'
_chemical_formula_sum            'C21 H24 Cl N O'
_chemical_formula_weight         341.86
_chemical_melting_point          202.0(10)
_chemical_name_common
'4-(4-chlorophenyl)-2-phenyl-N-hydroxy decahydroquinoline'
_chemical_name_systematic
;
4-(4-chlorophenyl)-2-phenyl-N-hydroxy decahydroquinoline

;
_space_group_IT_number           5
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  'C 2y'
_symmetry_space_group_name_H-M   'C 1 2 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                90.00
_cell_angle_beta                 90.279(12)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   19.532(3)
_cell_length_b                   5.3933(7)
_cell_length_c                   16.414(2)
_cell_measurement_reflns_used    1234
_cell_measurement_temperature    110(2)
_cell_measurement_theta_max      59.53
_cell_measurement_theta_min      4.53
_cell_volume                     1729.1(4)
_computing_cell_refinement
;
CELL-NOW (Sheldrick, 2003) and SAINT (BRUKER-NONIUS, 2003)
;
_computing_data_collection       'FRAMBO (BRUKER-NONIUS, 2003)'
_computing_data_reduction        'Bruker APEX2'
_computing_molecular_graphics    'X-SEED (Barbour, 2001)'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      110(2)
_diffrn_measured_fraction_theta_full 0.989
_diffrn_measured_fraction_theta_max 0.989
_diffrn_measurement_device_type  'BRUKER GADDS D8 Discover'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0591
_diffrn_reflns_av_sigmaI/netI    0.0687
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            6910
_diffrn_reflns_theta_full        59.99
_diffrn_reflns_theta_max         59.99
_diffrn_reflns_theta_min         2.69
_exptl_absorpt_coefficient_mu    1.994
_exptl_absorpt_correction_T_max  0.8897
_exptl_absorpt_correction_T_min  0.7815
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS; (Sheldrick, 2006)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.313
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             728
_exptl_crystal_size_max          0.13
_exptl_crystal_size_mid          0.07
_exptl_crystal_size_min          0.06
_refine_diff_density_max         0.199
_refine_diff_density_min         -0.274
_refine_diff_density_rms         0.051
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.05(2)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.047
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     217
_refine_ls_number_reflns         2353
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.047
_refine_ls_R_factor_all          0.0527
_refine_ls_R_factor_gt           0.0411
_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
[0.00000+1.00000exp(1.00(sinθ/λ)²)]/
[σ²(Fo²)+0.0000+0.0000*P+(0.0471P)²+0.0000sinθ/λ]
where P = 0.33333Fo² + 0.66667Fc²

;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0918
_refine_ls_wR_factor_ref         0.0953
_reflns_number_gt                1907
_reflns_number_total             2353
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c1ob05232b.txt
_cod_data_source_block           14b
_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 1555 2011-01-17 13:19:09Z saulius 

The following automatic conversions were performed:

'_chemical_melting_point' value '201-203' was changed to '202.0(10)'
- the average value was taken and precision was estimated.

Automatic conversion script
Id: cif_fix_values 1569 2011-02-09 13:29:24Z adriana 
;
_cod_original_cell_volume        1729.0(4)
_cod_original_sg_symbol_H-M      C2
_cod_database_code               7151873
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y, -z'
'x+1/2, y+1/2, z'
'-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
_atom_site_disorder_assembly
_atom_site_disorder_group
Cl1 Cl 0.09750(4) -0.01817(18) 0.50694(5) 0.0347(3) Uani 1 1 d . . .
O1 O 0.49176(12) 0.2251(5) 0.90721(14) 0.0281(6) Uani 1 1 d D . .
H1O H 0.5273 0.1374 0.8998 0.042 Uiso 1 1 d RD . .
C1 C 0.45266(18) 0.2473(7) 0.7735(2) 0.0225(8) Uani 1 1 d . . .
H1A H 0.4473 0.4282 0.7852 0.027 Uiso 1 1 calc R . .
N1 N 0.44353(14) 0.1075(5) 0.85030(17) 0.0211(7) Uani 1 1 d . . .
C4 C 0.32072(17) 0.0653(7) 0.8280(2) 0.0213(8) Uani 1 1 d . . .
H4A H 0.2750 0.0906 0.8524 0.026 Uiso 1 1 calc R . .
H4B H 0.3267 -0.1144 0.8180 0.026 Uiso 1 1 calc R . .
C3 C 0.32505(17) 0.2067(7) 0.7471(2) 0.0203(8) Uani 1 1 d . . .
H3A H 0.3206 0.3869 0.7603 0.024 Uiso 1 1 calc R . .
C7 C 0.53354(18) -0.0621(7) 0.7100(2) 0.0257(9) Uani 1 1 d . . .
H7A H 0.5803 -0.0827 0.6881 0.031 Uiso 1 1 calc R . .
H7B H 0.5281 -0.1775 0.7565 0.031 Uiso 1 1 calc R . .
C19 C 0.16427(16) 0.0448(7) 0.5744(2) 0.0214(9) Uani 1 1 d . . .
C21 C 0.22821(17) -0.0662(7) 0.6936(2) 0.0243(9) Uani 1 1 d . . .
H21A H 0.2363 -0.1780 0.7373 0.029 Uiso 1 1 calc R . .
C18 C 0.20306(18) 0.2546(7) 0.5653(2) 0.0272(9) Uani 1 1 d . . .
H18A H 0.1944 0.3655 0.5215 0.033 Uiso 1 1 calc R . .
C16 C 0.26836(18) 0.1452(7) 0.6867(2) 0.0209(8) Uani 1 1 d . . .
C13 C 0.35451(19) -0.1978(7) 1.1207(2) 0.0291(9) Uani 1 1 d . . .
H13A H 0.3496 -0.2739 1.1725 0.035 Uiso 1 1 calc R . .
C20 C 0.17615(18) -0.1178(7) 0.6376(2) 0.0252(9) Uani 1 1 d . . .
H20A H 0.1492 -0.2635 0.6430 0.030 Uiso 1 1 calc R . .
C12 C 0.31743(18) 0.0120(8) 1.1015(2) 0.0283(9) Uani 1 1 d . . .
H12A H 0.2868 0.0799 1.1404 0.034 Uiso 1 1 calc R . .
C17 C 0.25557(19) 0.3034(7) 0.6213(2) 0.0270(9) Uani 1 1 d . . .
H17A H 0.2830 0.4472 0.6146 0.032 Uiso 1 1 calc R . .
C9 C 0.40868(18) -0.0891(7) 0.6771(2) 0.0253(9) Uani 1 1 d . . .
H9A H 0.3752 -0.1205 0.6328 0.030 Uiso 1 1 calc R . .
H9B H 0.4004 -0.2121 0.7207 0.030 Uiso 1 1 calc R . .
C5 C 0.37589(17) 0.1558(7) 0.8870(2) 0.0208(8) Uani 1 1 d . . .
H5A H 0.3705 0.3386 0.8949 0.025 Uiso 1 1 calc R . .
C6 C 0.52400(18) 0.2035(7) 0.7394(2) 0.0264(9) Uani 1 1 d . . .
H6A H 0.5585 0.2404 0.7821 0.032 Uiso 1 1 calc R . .
H6B H 0.5319 0.3186 0.6933 0.032 Uiso 1 1 calc R . .
C15 C 0.40606(19) -0.1857(7) 0.9876(2) 0.0259(9) Uani 1 1 d . . .
H15A H 0.4359 -0.2563 0.9484 0.031 Uiso 1 1 calc R . .
C2 C 0.39740(17) 0.1693(7) 0.7107(2) 0.0215(8) Uani 1 1 d . . .
H2A H 0.4013 0.2863 0.6637 0.026 Uiso 1 1 calc R . .
C14 C 0.3989(2) -0.2968(7) 1.0639(2) 0.0282(9) Uani 1 1 d . . .
H14A H 0.4247 -0.4411 1.0768 0.034 Uiso 1 1 calc R . .
C10 C 0.36939(17) 0.0290(7) 0.9689(2) 0.0220(8) Uani 1 1 d . . .
C8 C 0.48120(17) -0.1243(7) 0.6441(2) 0.0271(9) Uani 1 1 d . . .
H8A H 0.4874 -0.2982 0.6262 0.032 Uiso 1 1 calc R . .
H8B H 0.4882 -0.0151 0.5964 0.032 Uiso 1 1 calc R . .
C11 C 0.32429(18) 0.1246(7) 1.0262(2) 0.0237(9) Uani 1 1 d . . .
H11A H 0.2980 0.2680 1.0136 0.028 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 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.3639 0.7018 '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
H1O O1 N1 101.0 . . ?
H1O O1 H1O 0.0 . . ?
N1 O1 H1O 101.0 . . ?
N1 C1 C6 110.4(3) . . ?
N1 C1 C2 110.0(3) . . ?
C6 C1 C2 110.5(3) . . ?
N1 C1 H1A 108.6 . . ?
C6 C1 H1A 108.6 . . ?
C2 C1 H1A 108.6 . . ?
O1 N1 C5 103.7(2) . . ?
O1 N1 C1 104.0(2) . . ?
C5 N1 C1 111.7(3) . . ?
C5 C4 C3 110.4(3) . . ?
C5 C4 H4A 109.6 . . ?
C3 C4 H4A 109.6 . . ?
C5 C4 H4B 109.6 . . ?
C3 C4 H4B 109.6 . . ?
H4A C4 H4B 108.1 . . ?
C16 C3 C4 114.4(3) . . ?
C16 C3 C2 112.6(3) . . ?
C4 C3 C2 108.8(3) . . ?
C16 C3 H3A 106.9 . . ?
C4 C3 H3A 106.9 . . ?
C2 C3 H3A 106.9 . . ?
C8 C7 C6 110.4(3) . . ?
C8 C7 H7A 109.6 . . ?
C6 C7 H7A 109.6 . . ?
C8 C7 H7B 109.6 . . ?
C6 C7 H7B 109.6 . . ?
H7A C7 H7B 108.1 . . ?
C18 C19 C20 121.1(3) . . ?
C18 C19 Cl1 120.3(3) . . ?
C20 C19 Cl1 118.6(3) . . ?
C16 C21 C20 121.3(3) . . ?
C16 C21 H21A 119.3 . . ?
C20 C21 H21A 119.3 . . ?
C19 C18 C17 119.2(3) . . ?
C19 C18 H18A 120.4 . . ?
C17 C18 H18A 120.4 . . ?
C21 C16 C17 117.8(3) . . ?
C21 C16 C3 122.5(3) . . ?
C17 C16 C3 119.8(3) . . ?
C12 C13 C14 119.6(3) . . ?
C12 C13 H13A 120.2 . . ?
C14 C13 H13A 120.2 . . ?
C19 C20 C21 119.3(3) . . ?
C19 C20 H20A 120.4 . . ?
C21 C20 H20A 120.4 . . ?
C13 C12 C11 120.7(3) . . ?
C13 C12 H12A 119.6 . . ?
C11 C12 H12A 119.6 . . ?
C16 C17 C18 121.3(4) . . ?
C16 C17 H17A 119.4 . . ?
C18 C17 H17A 119.4 . . ?
C2 C9 C8 112.3(3) . . ?
C2 C9 H9A 109.1 . . ?
C8 C9 H9A 109.1 . . ?
C2 C9 H9B 109.1 . . ?
C8 C9 H9B 109.1 . . ?
H9A C9 H9B 107.9 . . ?
N1 C5 C10 111.2(3) . . ?
N1 C5 C4 108.3(3) . . ?
C10 C5 C4 110.9(3) . . ?
N1 C5 H5A 108.8 . . ?
C10 C5 H5A 108.8 . . ?
C4 C5 H5A 108.8 . . ?
C1 C6 C7 112.1(3) . . ?
C1 C6 H6A 109.2 . . ?
C7 C6 H6A 109.2 . . ?
C1 C6 H6B 109.2 . . ?
C7 C6 H6B 109.2 . . ?
H6A C6 H6B 107.9 . . ?
C10 C15 C14 120.0(4) . . ?
C10 C15 H15A 120.0 . . ?
C14 C15 H15A 120.0 . . ?
C9 C2 C1 113.0(3) . . ?
C9 C2 C3 113.2(3) . . ?
C1 C2 C3 110.1(3) . . ?
C9 C2 H2A 106.7 . . ?
C1 C2 H2A 106.7 . . ?
C3 C2 H2A 106.7 . . ?
C13 C14 C15 120.3(4) . . ?
C13 C14 H14A 119.9 . . ?
C15 C14 H14A 119.9 . . ?
C11 C10 C15 119.1(3) . . ?
C11 C10 C5 119.3(3) . . ?
C15 C10 C5 121.6(3) . . ?
C7 C8 C9 109.9(3) . . ?
C7 C8 H8A 109.7 . . ?
C9 C8 H8A 109.7 . . ?
C7 C8 H8B 109.7 . . ?
C9 C8 H8B 109.7 . . ?
H8A C8 H8B 108.2 . . ?
C12 C11 C10 120.3(3) . . ?
C12 C11 H11A 119.8 . . ?
C10 C11 H11A 119.8 . . ?
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
Cl1 C19 1.740(3) . ?
O1 H1O 0.8499 . ?
O1 N1 1.468(3) . ?
O1 H1O 0.8499 . ?
C1 N1 1.481(4) . ?
C1 C6 1.523(5) . ?
C1 C2 1.546(5) . ?
C1 H1A 1.0000 . ?
N1 C5 1.478(4) . ?
C4 C5 1.526(5) . ?
C4 C3 1.535(5) . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C3 C16 1.518(5) . ?
C3 C2 1.550(5) . ?
C3 H3A 1.0000 . ?
C7 C8 1.523(5) . ?
C7 C6 1.523(5) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C19 C18 1.370(5) . ?
C19 C20 1.376(5) . ?
C21 C16 1.389(5) . ?
C21 C20 1.396(5) . ?
C21 H21A 0.9500 . ?
C18 C17 1.399(5) . ?
C18 H18A 0.9500 . ?
C16 C17 1.393(5) . ?
C13 C12 1.379(6) . ?
C13 C14 1.384(5) . ?
C13 H13A 0.9500 . ?
C20 H20A 0.9500 . ?
C12 C11 1.384(5) . ?
C12 H12A 0.9500 . ?
C17 H17A 0.9500 . ?
C9 C2 1.516(5) . ?
C9 C8 1.531(5) . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C5 C10 1.514(5) . ?
C5 H5A 1.0000 . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C15 C10 1.395(5) . ?
C15 C14 1.396(5) . ?
C15 H15A 0.9500 . ?
C2 H2A 1.0000 . ?
C14 H14A 0.9500 . ?
C10 C11 1.390(5) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C11 H11A 0.9500 . ?
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
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
H1O O1 N1 C5 152.3 . . . . ?
H1O O1 N1 C1 -90.8 . . . . ?
C6 C1 N1 O1 66.1(3) . . . . ?
C2 C1 N1 O1 -171.8(3) . . . . ?
C6 C1 N1 C5 177.2(3) . . . . ?
C2 C1 N1 C5 -60.6(4) . . . . ?
C5 C4 C3 C16 -175.1(3) . . . . ?
C5 C4 C3 C2 58.1(4) . . . . ?
C20 C19 C18 C17 0.0(5) . . . . ?
Cl1 C19 C18 C17 178.7(3) . . . . ?
C20 C21 C16 C17 -0.8(5) . . . . ?
C20 C21 C16 C3 179.6(3) . . . . ?
C4 C3 C16 C21 -17.4(5) . . . . ?
C2 C3 C16 C21 107.5(4) . . . . ?
C4 C3 C16 C17 163.0(3) . . . . ?
C2 C3 C16 C17 -72.0(4) . . . . ?
C18 C19 C20 C21 0.6(5) . . . . ?
Cl1 C19 C20 C21 -178.1(3) . . . . ?
C16 C21 C20 C19 -0.2(5) . . . . ?
C14 C13 C12 C11 -0.1(5) . . . . ?
C21 C16 C17 C18 1.4(5) . . . . ?
C3 C16 C17 C18 -179.0(4) . . . . ?
C19 C18 C17 C16 -1.0(6) . . . . ?
O1 N1 C5 C10 -63.9(3) . . . . ?
C1 N1 C5 C10 -175.3(3) . . . . ?
O1 N1 C5 C4 174.0(3) . . . . ?
C1 N1 C5 C4 62.6(4) . . . . ?
C3 C4 C5 N1 -61.2(4) . . . . ?
C3 C4 C5 C10 176.5(3) . . . . ?
N1 C1 C6 C7 68.0(4) . . . . ?
C2 C1 C6 C7 -53.9(4) . . . . ?
C8 C7 C6 C1 59.0(4) . . . . ?
C8 C9 C2 C1 -52.1(4) . . . . ?
C8 C9 C2 C3 -178.1(3) . . . . ?
N1 C1 C2 C9 -71.6(4) . . . . ?
C6 C1 C2 C9 50.5(4) . . . . ?
N1 C1 C2 C3 56.1(4) . . . . ?
C6 C1 C2 C3 178.2(3) . . . . ?
C16 C3 C2 C9 -55.3(4) . . . . ?
C4 C3 C2 C9 72.6(4) . . . . ?
C16 C3 C2 C1 177.2(3) . . . . ?
C4 C3 C2 C1 -54.9(4) . . . . ?
C12 C13 C14 C15 -0.2(5) . . . . ?
C10 C15 C14 C13 1.3(5) . . . . ?
C14 C15 C10 C11 -2.1(5) . . . . ?
C14 C15 C10 C5 179.8(3) . . . . ?
N1 C5 C10 C11 154.6(3) . . . . ?
C4 C5 C10 C11 -84.7(4) . . . . ?
N1 C5 C10 C15 -27.3(4) . . . . ?
C4 C5 C10 C15 93.4(4) . . . . ?
C6 C7 C8 C9 -58.4(4) . . . . ?
C2 C9 C8 C7 55.5(4) . . . . ?
C13 C12 C11 C10 -0.7(5) . . . . ?
C15 C10 C11 C12 1.8(5) . . . . ?
C5 C10 C11 C12 180.0(3) . . . . ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 30653500
