#------------------------------------------------------------------------------
#$Date: 2017-10-13 03:48:21 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201957 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/01/22/2012228.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided by IUCr Journals, http://journals.iucr.org/.
#
# The file may be used within the scientific community so long as
# proper attribution is given to the journal article from which the
# data were obtained.
#
data_2012228
loop_
_publ_author_name
'Usman, Anwar'
'Razak, Ibrahim Abdul'
'Chantrapromma, Suchada'
'Fun, Hoong-Kun'
'Sarkar, Tarun K.'
'Basak, Sankar'
'Nigam, Gur Dayal'
_publ_section_title
;Methyl
 (SR)-10-chloro-1,2,3,4,5,6-hexahydro-6-hydroxy-8-methoxy-1-methyl-1,9-phenanthroline-6-carboxylate
;
_journal_issue                   9
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              1116
_journal_page_last               1117
_journal_paper_doi               10.1107/S0108270101010770
_journal_volume                  57
_journal_year                    2001
_chemical_formula_moiety         'C16 H19 Cl N2 O4'
_chemical_formula_sum            'C16 H19 Cl N2 O4'
_chemical_formula_weight         338.78
_chemical_melting_point          426
_chemical_name_systematic
;
Methyl (SR)-10-chloro-1,2,3,4,5,6-hexahydro-6-hydroxy-8-methoxy-1-methyl-
1,9-phenanthroline-6-carboxylate
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_audit_creation_method           SHELXL97
_cell_angle_alpha                100.5740(10)
_cell_angle_beta                 101.7510(10)
_cell_angle_gamma                111.8820(10)
_cell_formula_units_Z            2
_cell_length_a                   9.2081(4)
_cell_length_b                   9.4835(4)
_cell_length_c                   11.1287(6)
_cell_measurement_reflns_used    3323
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      28.32
_cell_measurement_theta_min      1.95
_cell_volume                     846.14(7)
_computing_cell_refinement       'SAINT (Siemens, 1996)'
_computing_data_collection       'SMART (Siemens, 1996)'
_computing_data_reduction        SAINT
_computing_molecular_graphics    SHELXTL
_computing_publication_material
'SHELXTL, PARST95 (Nardelli, 1995) and PLATON (Spek, 1990)'
_computing_structure_refinement  SHELXTL
_computing_structure_solution    'SHELXTL (Sheldrick, 1997)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean 8.33
_diffrn_measured_fraction_theta_full .955
_diffrn_measured_fraction_theta_max .955
_diffrn_measurement_device_type  'Siemens SMART CCD area-detector'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     .71073
_diffrn_reflns_av_R_equivalents  .057
_diffrn_reflns_av_sigmaI/netI    .110
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            6088
_diffrn_reflns_theta_full        28.24
_diffrn_reflns_theta_max         28.24
_diffrn_reflns_theta_min         1.95
_diffrn_standards_decay_%        negligible
_exptl_absorpt_coefficient_mu    .247
_exptl_absorpt_correction_T_max  .948
_exptl_absorpt_correction_T_min  .895
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 1996)'
_exptl_crystal_colour            'yellowish green'
_exptl_crystal_density_diffrn    1.330
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       slab
_exptl_crystal_F_000             356
_exptl_crystal_size_max          .46
_exptl_crystal_size_mid          .36
_exptl_crystal_size_min          .22
_refine_diff_density_max         .63
_refine_diff_density_min         -.62
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   .939
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     212
_refine_ls_number_reflns         3990
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      .939
_refine_ls_R_factor_all          .111
_refine_ls_R_factor_gt           .076
_refine_ls_shift/su_max          <0.001
_refine_ls_shift/su_mean         .000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w = 1/[σ²(Fo²)+(0.1071P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_ref         .209
_reflns_number_gt                2299
_reflns_number_total             3990
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            sk1492.cif
_cod_data_source_block           I
_cod_depositor_comments
;
The following automatic conversions were performed:

'_chemical_melting_point' value '426K' was changed to '426' - the
value should be numeric and without a unit designator.

Automatic conversion script
Id: cif_fix_values 1646 2011-03-28 12:23:43Z adriana 

The following automatic conversions were performed:

'_chemical_melting_point' value '426K' was changed to '426' - the
value should be numeric and without a unit designator.

Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_original_sg_symbol_H-M      P-1
_cod_database_code               2012228
_cod_database_fobs_code          2012228
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
loop_
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
_atom_site_type_symbol
Cl1 .45819(11) .21311(9) .18714(8) .0550(3) Uani d . 1 . . Cl
O1 .3028(2) .7970(3) .3657(2) .0503(6) Uani d . 1 . . O
H1A .3411 .8839 .4188 .075 Uiso calc R 1 . . H
O2 -.0171(3) .3112(3) .0170(2) .0575(6) Uani d . 1 . . O
O3 .5669(3) .8382(2) .2006(2) .0521(6) Uani d . 1 . . O
O4 .6409(3) 1.0135(3) .3897(2) .0564(7) Uani d . 1 . . O
N1 .2167(3) .2805(3) .0998(2) .0391(6) Uani d . 1 . . N
N2 .7440(3) .5413(3) .3051(3) .0481(7) Uani d . 1 . . N
C1 .3702(4) .3479(3) .1796(3) .0362(6) Uani d . 1 . . C
C2 .4532(3) .5035(3) .2557(3) .0323(6) Uani d . 1 . . C
C3 .6239(3) .5831(3) .3428(3) .0361(6) Uani d . 1 . . C
C4 .9080(5) .6318(8) .3933(5) .108(2) Uani d D 1 . . C
H4A .9669 .5658 .3879 .130 Uiso calc R 1 . . H
H4B .9632 .7219 .3640 .130 Uiso calc R 1 . . H
C5 .9225(6) .6899(9) .5249(5) .149(3) Uani d D 1 . . C
H5A 1.0357 .7648 .5682 .179 Uiso calc R 1 . . H
H5B .9002 .6015 .5614 .179 Uiso calc R 1 . . H
C6 .8205(4) .7653(5) .5543(4) .0600(10) Uani d D 1 . . C
H6A .8735 .8766 .5587 .072 Uiso calc R 1 . . H
H6B .8065 .7587 .6374 .072 Uiso calc R 1 . . H
C7 .6541(3) .6888(3) .4544(3) .0372(7) Uani d . 1 . . C
C8 .5202(4) .7338(4) .4785(3) .0398(7) Uani d . 1 . . C
H8A .5668 .8331 .5459 .048 Uiso calc R 1 . . H
H8B .4444 .6526 .5056 .048 Uiso calc R 1 . . H
C9 .4305(3) .7510(3) .3549(3) .0362(7) Uani d . 1 . . C
C10 .3563(3) .5894(3) .2559(3) .0315(6) Uani d . 1 . . C
C11 .1993(4) .5246(4) .1770(3) .0401(7) Uani d . 1 . . C
H11A .1362 .5816 .1761 .048 Uiso calc R 1 . . H
C12 .1361(3) .3693(4) .0974(3) .0392(7) Uani d . 1 . . C
C13 .7499(5) .5374(5) .1754(4) .0674(11) Uani d . 1 . . C
H13A .8091 .4777 .1515 .101 Uiso calc R 1 . . H
H13B .8043 .6437 .1708 .101 Uiso calc R 1 . . H
H13C .6404 .4883 .1179 .101 Uiso calc R 1 . . H
C14 .5584(4) .8815(3) .3185(3) .0375(7) Uani d . 1 . . C
C15 .6896(6) .9556(5) .1650(4) .0739(12) Uani d . 1 . . C
H15A .6901 .9110 .0805 .111 Uiso calc R 1 . . H
H15B .7954 .9884 .2247 .111 Uiso calc R 1 . . H
H15C .6650 1.0456 .1663 .111 Uiso calc R 1 . . H
C16 -.0894(5) .1510(4) -.0618(4) .0714(12) Uani d . 1 . . C
H16A -.1965 .1265 -.1155 .107 Uiso calc R 1 . . H
H16B -.0984 .0810 -.0086 .107 Uiso calc R 1 . . H
H16C -.0219 .1379 -.1142 .107 Uiso calc R 1 . . H
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C .0033 .0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H .0000 .0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N .0061 .0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O .0106 .0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl .1484 .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
_geom_angle_publ_flag
C9 O1 H1A 109.5 ?
C12 O2 C16 118.4(3) ?
C14 O3 C15 115.9(3) ?
C12 N1 C1 116.7(2) ?
C3 N2 C4 113.9(3) yes
C3 N2 C13 116.8(3) ?
C4 N2 C13 109.3(3) ?
N1 C1 C2 126.0(3) ?
N1 C1 Cl1 112.8(2) ?
C2 C1 Cl1 121.1(2) ?
C1 C2 C10 114.3(2) ?
C1 C2 C3 127.6(3) ?
C10 C2 C3 117.9(2) ?
C7 C3 N2 124.0(3) yes
C7 C3 C2 117.7(2) ?
N2 C3 C2 118.3(2) ?
C5 C4 N2 117.4(4) ?
C5 C4 H4A 108.0 ?
N2 C4 H4A 108.0 ?
C5 C4 H4B 108.0 ?
N2 C4 H4B 108.0 ?
H4A C4 H4B 107.2 ?
C4 C5 C6 117.8(5) ?
C4 C5 H5A 107.9 ?
C6 C5 H5A 107.9 ?
C4 C5 H5B 107.9 ?
C6 C5 H5B 107.9 ?
H5A C5 H5B 107.2 ?
C5 C6 C7 111.4(3) ?
C5 C6 H6A 109.3 ?
C7 C6 H6A 109.3 ?
C5 C6 H6B 109.3 ?
C7 C6 H6B 109.3 ?
H6A C6 H6B 108.0 ?
C3 C7 C8 119.0(3) yes
C3 C7 C6 121.5(3) ?
C8 C7 C6 119.5(3) ?
C7 C8 C9 108.4(2) yes
C7 C8 H8A 110.0 ?
C9 C8 H8A 110.0 ?
C7 C8 H8B 110.0 ?
C9 C8 H8B 110.0 ?
H8A C8 H8B 108.4 ?
O1 C9 C8 114.1(2) ?
O1 C9 C10 108.4(2) yes
C8 C9 C10 106.8(2) yes
O1 C9 C14 107.7(2) yes
C8 C9 C14 106.9(2) ?
C10 C9 C14 113.2(2) ?
C11 C10 C2 121.0(3) ?
C11 C10 C9 121.9(2) ?
C2 C10 C9 116.9(2) ?
C10 C11 C12 117.9(3) ?
C10 C11 H11A 121.0 ?
C12 C11 H11A 121.0 ?
N1 C12 O2 120.1(3) ?
N1 C12 C11 123.5(3) ?
O2 C12 C11 116.4(3) ?
N2 C13 H13A 109.5 ?
N2 C13 H13B 109.5 ?
H13A C13 H13B 109.5 ?
N2 C13 H13C 109.5 ?
H13A C13 H13C 109.5 ?
H13B C13 H13C 109.5 ?
O4 C14 O3 122.6(3) ?
O4 C14 C9 122.9(3) ?
O3 C14 C9 114.5(2) ?
O3 C15 H15A 109.5 ?
O3 C15 H15B 109.5 ?
H15A C15 H15B 109.5 ?
O3 C15 H15C 109.5 ?
H15A C15 H15C 109.5 ?
H15B C15 H15C 109.5 ?
O2 C16 H16A 109.5 ?
O2 C16 H16B 109.5 ?
H16A C16 H16B 109.5 ?
O2 C16 H16C 109.5 ?
H16A C16 H16C 109.5 ?
H16B C16 H16C 109.5 ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
Cl1 C1 . 1.755(3) ?
O1 C9 . 1.417(3) ?
O1 H1A . .8200 ?
O2 C12 . 1.348(3) ?
O2 C16 . 1.428(4) ?
O3 C14 . 1.329(3) ?
O3 C15 . 1.442(4) ?
O4 C14 . 1.206(3) ?
N1 C12 . 1.314(4) yes
N1 C1 . 1.343(4) yes
N2 C3 . 1.418(4) yes
N2 C4 . 1.450(5) yes
N2 C13 . 1.451(5) ?
C1 C2 . 1.385(4) ?
C2 C10 . 1.415(4) yes
C2 C3 . 1.485(4) yes
C3 C7 . 1.349(4) yes
C4 C5 . 1.426(4) ?
C4 H4A . .9700 ?
C4 H4B . .9700 ?
C5 C6 . 1.429(4) ?
C5 H5A . .9700 ?
C5 H5B . .9700 ?
C6 C7 . 1.514(4) yes
C6 H6A . .9700 ?
C6 H6B . .9700 ?
C7 C8 . 1.503(4) yes
C8 C9 . 1.524(4) yes
C8 H8A . .9700 ?
C8 H8B . .9700 ?
C9 C10 . 1.524(4) yes
C9 C14 . 1.541(4) ?
C10 C11 . 1.364(4) ?
C11 C12 . 1.402(4) ?
C11 H11A . .9300 ?
C13 H13A . .9600 ?
C13 H13B . .9600 ?
C13 H13C . .9600 ?
C15 H15A . .9600 ?
C15 H15B . .9600 ?
C15 H15C . .9600 ?
C16 H16A . .9600 ?
C16 H16B . .9600 ?
C16 H16C . .9600 ?
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_publ_flag
C12 N1 C1 C2 -2.6(4) ?
C12 N1 C1 Cl1 173.8(2) ?
N1 C1 C2 C10 6.8(4) ?
Cl1 C1 C2 C10 -169.3(2) ?
N1 C1 C2 C3 -178.5(3) ?
Cl1 C1 C2 C3 5.4(4) ?
C4 N2 C3 C7 -4.5(5) ?
C13 N2 C3 C7 -133.5(3) ?
C4 N2 C3 C2 176.8(4) ?
C13 N2 C3 C2 47.8(4) ?
C1 C2 C3 C7 -142.8(3) ?
C10 C2 C3 C7 31.6(4) yes
C1 C2 C3 N2 35.9(4) yes
C10 C2 C3 N2 -149.6(3) yes
C3 N2 C4 C5 28.8(8) ?
C13 N2 C4 C5 161.4(6) ?
N2 C4 C5 C6 -46.3(10) ?
C4 C5 C6 C7 35.1(9) ?
N2 C3 C7 C8 174.7(3) ?
C2 C3 C7 C8 -6.6(4) ?
N2 C3 C7 C6 -4.0(5) ?
C2 C3 C7 C6 174.7(3) ?
C5 C6 C7 C3 -10.9(6) ?
C5 C6 C7 C8 170.4(4) ?
C3 C7 C8 C9 -40.5(4) ?
C6 C7 C8 C9 138.3(3) ?
C7 C8 C9 O1 -178.6(2) ?
C7 C8 C9 C10 61.6(3) ?
C7 C8 C9 C14 -59.7(3) ?
C1 C2 C10 C11 -5.8(4) ?
C3 C2 C10 C11 179.1(3) ?
C1 C2 C10 C9 169.5(2) ?
C3 C2 C10 C9 -5.6(4) ?
O1 C9 C10 C11 12.0(4) ?
C8 C9 C10 C11 135.3(3) ?
C14 C9 C10 C11 -107.4(3) ?
O1 C9 C10 C2 -163.3(2) ?
C8 C9 C10 C2 -40.0(3) ?
C14 C9 C10 C2 77.4(3) ?
C2 C10 C11 C12 1.0(4) ?
C9 C10 C11 C12 -174.0(3) ?
C1 N1 C12 O2 178.1(3) ?
C1 N1 C12 C11 -3.1(4) yes
C16 O2 C12 N1 1.7(4) yes
C16 O2 C12 C11 -177.2(3) ?
C10 C11 C12 N1 3.8(5) ?
C10 C11 C12 O2 -177.4(3) ?
C15 O3 C14 O4 4.1(5) ?
C15 O3 C14 C9 -177.8(3) ?
O1 C9 C14 O4 67.0(3) ?
C8 C9 C14 O4 -56.0(3) ?
C10 C9 C14 O4 -173.2(3) yes
O1 C9 C14 O3 -111.1(3) ?
C8 C9 C14 O3 125.9(3) ?
C10 C9 C14 O3 8.7(3) ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 21107375
