#------------------------------------------------------------------------------
#$Date: 2016-02-20 22:30:07 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176789 $
#$URL: svn://www.crystallography.net/cod/cif/2/22/36/2223640.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_2223640
loop_
_publ_author_name
'Ravichandran, K.'
'Ramesh, P.'
'Sakthivel, P.'
'Ponnuswamy, S.'
'Ponnuswamy, M. N.'
_publ_section_title
1-Chloroacetyl-r-2,c-6-bis(4-methoxyphenyl)-t-3-methylpiperidin-4-one
_journal_coeditor_code           BT5090
_journal_issue                   11
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o2883
_journal_paper_doi               10.1107/S1600536809043281
_journal_volume                  65
_journal_year                    2009
_chemical_formula_iupac          'C22 H24 Cl N O4'
_chemical_formula_moiety         'C22 H24 Cl N O4'
_chemical_formula_sum            'C22 H24 Cl N O4'
_chemical_formula_weight         401.87
_chemical_name_systematic
1-Chloroacetyl-r-2,c-6-bis(4-methoxyphenyl)-t-3-methylpiperidin-4-one
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                99.729(5)
_cell_angle_beta                 93.665(5)
_cell_angle_gamma                90.112(6)
_cell_formula_units_Z            4
_cell_length_a                   8.9147(8)
_cell_length_b                   11.9648(10)
_cell_length_c                   19.1365(16)
_cell_measurement_reflns_used    4567
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      28.36
_cell_measurement_theta_min      1.08
_cell_volume                     2007.5(3)
_computing_cell_refinement       'SAINT (Bruker, 2004)'
_computing_data_collection       'APEX2 (Bruker, 2004)'
_computing_data_reduction        'SAINT (Bruker, 2004)'
_computing_molecular_graphics    'ORTEP-3 (Farrugia, 1997)'
_computing_publication_material
'SHELXL97 (Sheldrick, 2008) and PLATON (Spek, 2009)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Bruker Kappa APEXII area-detector'
_diffrn_measurement_method       'ω and φ'
_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  0.0425
_diffrn_reflns_av_sigmaI/netI    0.0460
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            37036
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         28.36
_diffrn_reflns_theta_min         1.08
_diffrn_standards_decay_%        0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.218
_exptl_absorpt_correction_T_max  0.970
_exptl_absorpt_correction_T_min  0.968
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 2001)'
_exptl_crystal_colour            Colorless
_exptl_crystal_density_diffrn    1.330
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Block
_exptl_crystal_F_000             848
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.14
_refine_diff_density_max         0.486
_refine_diff_density_min         -0.366
_refine_ls_extinction_coef       0.0045(11)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL97 (Sheldrick, 2008)'
_refine_ls_goodness_of_fit_ref   1.046
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     512
_refine_ls_number_reflns         9971
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.046
_refine_ls_R_factor_all          0.1015
_refine_ls_R_factor_gt           0.0539
_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)+(0.0715P)²+0.4246P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1401
_refine_ls_wR_factor_ref         0.1640
_reflns_number_gt                5739
_reflns_number_total             9971
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            bt5090.cif
_cod_data_source_block           I
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic'
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 'Multi-scan' changed
to 'multi-scan' 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 

The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic'
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 'Multi-scan'
changed to 'multi-scan' 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_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_database_code               2223640
_cod_database_fobs_code          2223640
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
loop_
_atom_site_type_symbol
_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
Cl Cl1A 0.69594(8) 0.10702(6) 0.06473(4) 0.0702(2) Uani d . 1 . .
O O1A 0.65647(19) 0.09415(15) 0.21138(9) 0.0626(5) Uani d . 1 . .
O O2A 0.7515(2) -0.36334(16) 0.42043(11) 0.0770(6) Uani d . 1 . .
O O3A 1.2325(2) 0.12592(16) 0.38722(10) 0.0706(5) Uani d . 1 . .
O O4A 1.1117(2) -0.44641(14) 0.05999(10) 0.0697(5) Uani d . 1 . .
N N1A 0.8822(2) 0.02377(14) 0.24329(9) 0.0446(4) Uani d . 1 . .
C C2A 0.8500(3) 0.04894(19) 0.31906(12) 0.0494(5) Uani d . 1 . .
H H2A 0.7556 0.0908 0.3214 0.059 Uiso calc R 1 . .
C C3A 0.9715(3) 0.1301(2) 0.35698(14) 0.0578(6) Uani d . 1 . .
H H3A 0.9639 0.2009 0.3388 0.069 Uiso calc R 1 . .
H H3B 0.9541 0.1463 0.4072 0.069 Uiso calc R 1 . .
C C4A 1.1273(3) 0.08538(18) 0.34847(13) 0.0512(6) Uani d . 1 . .
C C5A 1.1443(2) -0.01490(19) 0.29002(13) 0.0497(5) Uani d . 1 . .
H H5A 1.1169 -0.0824 0.3094 0.060 Uiso calc R 1 . .
C C6A 1.0360(2) -0.01290(17) 0.22340(12) 0.0449(5) Uani d . 1 . .
H H6A 1.0759 0.0428 0.1971 0.054 Uiso calc R 1 . .
C C7A 0.7816(3) 0.06039(18) 0.19605(12) 0.0475(5) Uani d . 1 . .
C C8A 0.8334(3) 0.0573(2) 0.12192(13) 0.0605(6) Uani d . 1 . .
H H8A 0.8585 -0.0199 0.1022 0.073 Uiso calc R 1 . .
H H8B 0.9238 0.1036 0.1247 0.073 Uiso calc R 1 . .
C C9A 0.8240(2) -0.05747(19) 0.35050(11) 0.0453(5) Uani d . 1 . .
C C10A 0.7107(3) -0.1336(2) 0.32057(13) 0.0574(6) Uani d . 1 . .
H H10A 0.6485 -0.1167 0.2829 0.069 Uiso calc R 1 . .
C C11A 0.6880(3) -0.2336(2) 0.34529(14) 0.0631(7) Uani d . 1 . .
H H11A 0.6117 -0.2835 0.3241 0.076 Uiso calc R 1 . .
C C12A 0.7778(3) -0.2598(2) 0.40118(13) 0.0563(6) Uani d . 1 . .
C C13A 0.8878(3) -0.1850(2) 0.43326(13) 0.0579(6) Uani d . 1 . .
H H13A 0.9478 -0.2014 0.4717 0.070 Uiso calc R 1 . .
C C14A 0.9092(3) -0.0844(2) 0.40798(12) 0.0551(6) Uani d . 1 . .
H H14A 0.9833 -0.0336 0.4305 0.066 Uiso calc R 1 . .
C C15A 0.8486(4) -0.3965(3) 0.47465(18) 0.0905(10) Uani d . 1 . .
H H15A 0.9501 -0.3984 0.4606 0.136 Uiso calc R 1 . .
H H15B 0.8193 -0.4706 0.4823 0.136 Uiso calc R 1 . .
H H15C 0.8420 -0.3432 0.5178 0.136 Uiso calc R 1 . .
C C16A 1.3063(3) -0.0307(3) 0.27004(17) 0.0746(8) Uani d . 1 . .
H H16A 1.3329 0.0267 0.2434 0.112 Uiso calc R 1 . .
H H16B 1.3165 -0.1042 0.2417 0.112 Uiso calc R 1 . .
H H16C 1.3716 -0.0246 0.3124 0.112 Uiso calc R 1 . .
C C17A 1.0383(2) -0.12792(17) 0.17620(11) 0.0420(5) Uani d . 1 . .
C C18A 1.1144(3) -0.1434(2) 0.11456(13) 0.0537(6) Uani d . 1 . .
H H18A 1.1528 -0.0806 0.0986 0.064 Uiso calc R 1 . .
C C19A 1.1343(3) -0.2505(2) 0.07620(13) 0.0564(6) Uani d . 1 . .
H H19A 1.1851 -0.2591 0.0347 0.068 Uiso calc R 1 . .
C C20A 1.0794(3) -0.34451(19) 0.09928(12) 0.0498(5) Uani d . 1 . .
C C21A 0.9971(3) -0.33057(19) 0.15832(13) 0.0544(6) Uani d . 1 . .
H H21A 0.9544 -0.3932 0.1727 0.065 Uiso calc R 1 . .
C C22A 0.9780(3) -0.22299(19) 0.19627(13) 0.0506(5) Uani d . 1 . .
H H22A 0.9230 -0.2146 0.2365 0.061 Uiso calc R 1 . .
C C23A 1.0734(4) -0.5463(2) 0.08604(16) 0.0838(9) Uani d . 1 . .
H H23A 1.1205 -0.5439 0.1328 0.126 Uiso calc R 1 . .
H H23B 1.1075 -0.6115 0.0549 0.126 Uiso calc R 1 . .
H H23C 0.9663 -0.5511 0.0880 0.126 Uiso calc R 1 . .
Cl Cl1B 0.18993(8) 0.15752(6) 0.06531(4) 0.0739(2) Uani d . 1 . .
O O1B 0.15794(18) 0.24812(15) 0.21225(9) 0.0618(5) Uani d . 1 . .
O O2B 0.2506(2) 0.81846(16) 0.42158(11) 0.0777(6) Uani d . 1 . .
O O3B 0.7357(2) 0.31515(16) 0.38623(10) 0.0720(5) Uani d . 1 . .
O O4B 0.5886(3) 0.70404(15) 0.05185(10) 0.0773(6) Uani d . 1 . .
N N1B 0.38311(19) 0.33705(14) 0.24239(10) 0.0452(4) Uani d . 1 . .
C C2B 0.3520(3) 0.35249(19) 0.31822(12) 0.0491(5) Uani d . 1 . .
H H2B 0.2580 0.3113 0.3210 0.059 Uiso calc R 1 . .
C C3B 0.4754(3) 0.2927(2) 0.35614(14) 0.0587(6) Uani d . 1 . .
H H3C 0.4591 0.3042 0.4065 0.070 Uiso calc R 1 . .
H H3D 0.4680 0.2119 0.3383 0.070 Uiso calc R 1 . .
C C4B 0.6295(3) 0.33301(19) 0.34681(13) 0.0531(6) Uani d . 1 . .
C C5B 0.6454(2) 0.40160(19) 0.28828(13) 0.0512(6) Uani d . 1 . .
H H5B 0.6176 0.4794 0.3076 0.061 Uiso calc R 1 . .
C C6B 0.5369(2) 0.36252(18) 0.22178(12) 0.0462(5) Uani d . 1 . .
H H6B 0.5764 0.2925 0.1955 0.055 Uiso calc R 1 . .
C C7B 0.2822(3) 0.27392(17) 0.19570(12) 0.0472(5) Uani d . 1 . .
C C8B 0.3329(3) 0.2340(2) 0.12212(13) 0.0582(6) Uani d . 1 . .
H H8C 0.4199 0.1860 0.1251 0.070 Uiso calc R 1 . .
H H8D 0.3630 0.2991 0.1020 0.070 Uiso calc R 1 . .
C C9B 0.3264(2) 0.47558(19) 0.35026(11) 0.0460(5) Uani d . 1 . .
C C10B 0.2110(3) 0.5346(2) 0.32129(13) 0.0567(6) Uani d . 1 . .
H H10B 0.1481 0.4968 0.2841 0.068 Uiso calc R 1 . .
C C11B 0.1870(3) 0.6480(2) 0.34620(14) 0.0630(7) Uani d . 1 . .
H H11B 0.1093 0.6857 0.3255 0.076 Uiso calc R 1 . .
C C12B 0.2780(3) 0.7051(2) 0.40158(13) 0.0571(6) Uani d . 1 . .
C C13B 0.3896(3) 0.6475(2) 0.43301(13) 0.0592(6) Uani d . 1 . .
H H13B 0.4497 0.6847 0.4714 0.071 Uiso calc R 1 . .
C C14B 0.4119(3) 0.5341(2) 0.40725(13) 0.0559(6) Uani d . 1 . .
H H14B 0.4873 0.4960 0.4292 0.067 Uiso calc R 1 . .
C C15B 0.3483(4) 0.8816(3) 0.47489(19) 0.0936(10) Uani d . 1 . .
H H15D 0.3416 0.8530 0.5186 0.140 Uiso calc R 1 . .
H H15E 0.3202 0.9599 0.4817 0.140 Uiso calc R 1 . .
H H15F 0.4497 0.8747 0.4607 0.140 Uiso calc R 1 . .
C C16B 0.8068(3) 0.4073(3) 0.26829(17) 0.0766(8) Uani d . 1 . .
H H16D 0.8720 0.4253 0.3106 0.115 Uiso calc R 1 . .
H H16E 0.8165 0.4650 0.2395 0.115 Uiso calc R 1 . .
H H16F 0.8339 0.3354 0.2421 0.115 Uiso calc R 1 . .
C C17B 0.5366(2) 0.45185(17) 0.17413(12) 0.0442(5) Uani d . 1 . .
C C18B 0.6123(3) 0.4349(2) 0.11269(13) 0.0562(6) Uani d . 1 . .
H H18B 0.6545 0.3645 0.0979 0.067 Uiso calc R 1 . .
C C19B 0.6272(3) 0.5191(2) 0.07250(14) 0.0610(6) Uani d . 1 . .
H H19B 0.6778 0.5050 0.0310 0.073 Uiso calc R 1 . .
C C20B 0.5665(3) 0.6245(2) 0.09421(13) 0.0531(6) Uani d . 1 . .
C C21B 0.4870(3) 0.6429(2) 0.15428(14) 0.0560(6) Uani d . 1 . .
H H21B 0.4429 0.7128 0.1684 0.067 Uiso calc R 1 . .
C C22B 0.4730(3) 0.55669(19) 0.19369(13) 0.0513(6) Uani d . 1 . .
H H22B 0.4195 0.5699 0.2344 0.062 Uiso calc R 1 . .
C C23B 0.5585(4) 0.8176(2) 0.08017(17) 0.0823(9) Uani d . 1 . .
H H23D 0.4528 0.8258 0.0862 0.124 Uiso calc R 1 . .
H H23E 0.5889 0.8660 0.0483 0.124 Uiso calc R 1 . .
H H23F 0.6134 0.8383 0.1254 0.124 Uiso calc R 1 . .
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_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C12A O2A C15A . . 117.9(2) ?
C20A O4A C23A . . 118.0(2) ?
C7A N1A C2A . . 117.15(18) ?
C7A N1A C6A . . 121.55(18) ?
C2A N1A C6A . . 119.48(17) ?
N1A C2A C3A . . 107.47(19) ?
N1A C2A C9A . . 112.76(17) ?
C3A C2A C9A . . 116.32(19) ?
N1A C2A H2A . . 106.6 ?
C3A C2A H2A . . 106.6 ?
C9A C2A H2A . . 106.6 ?
C4A C3A C2A . . 113.41(19) ?
C4A C3A H3A . . 108.9 ?
C2A C3A H3A . . 108.9 ?
C4A C3A H3B . . 108.9 ?
C2A C3A H3B . . 108.9 ?
H3A C3A H3B . . 107.7 ?
O3A C4A C3A . . 121.6(2) ?
O3A C4A C5A . . 122.0(2) ?
C3A C4A C5A . . 116.36(19) ?
C4A C5A C16A . . 112.2(2) ?
C4A C5A C6A . . 113.58(18) ?
C16A C5A C6A . . 111.3(2) ?
C4A C5A H5A . . 106.4 ?
C16A C5A H5A . . 106.4 ?
C6A C5A H5A . . 106.4 ?
N1A C6A C17A . . 113.52(17) ?
N1A C6A C5A . . 111.62(18) ?
C17A C6A C5A . . 108.61(17) ?
N1A C6A H6A . . 107.6 ?
C17A C6A H6A . . 107.6 ?
C5A C6A H6A . . 107.6 ?
O1A C7A N1A . . 123.0(2) ?
O1A C7A C8A . . 121.1(2) ?
N1A C7A C8A . . 115.8(2) ?
C7A C8A Cl1A . . 112.47(17) ?
C7A C8A H8A . . 109.1 ?
Cl1A C8A H8A . . 109.1 ?
C7A C8A H8B . . 109.1 ?
Cl1A C8A H8B . . 109.1 ?
H8A C8A H8B . . 107.8 ?
C14A C9A C10A . . 116.9(2) ?
C14A C9A C2A . . 123.3(2) ?
C10A C9A C2A . . 119.7(2) ?
C11A C10A C9A . . 121.6(2) ?
C11A C10A H10A . . 119.2 ?
C9A C10A H10A . . 119.2 ?
C12A C11A C10A . . 120.2(2) ?
C12A C11A H11A . . 119.9 ?
C10A C11A H11A . . 119.9 ?
C13A C12A C11A . . 119.7(2) ?
C13A C12A O2A . . 124.0(2) ?
C11A C12A O2A . . 116.3(2) ?
C12A C13A C14A . . 119.5(2) ?
C12A C13A H13A . . 120.3 ?
C14A C13A H13A . . 120.3 ?
C9A C14A C13A . . 122.1(2) ?
C9A C14A H14A . . 119.0 ?
C13A C14A H14A . . 119.0 ?
O2A C15A H15A . . 109.5 ?
O2A C15A H15B . . 109.5 ?
H15A C15A H15B . . 109.5 ?
O2A C15A H15C . . 109.5 ?
H15A C15A H15C . . 109.5 ?
H15B C15A H15C . . 109.5 ?
C5A C16A H16A . . 109.5 ?
C5A C16A H16B . . 109.5 ?
H16A C16A H16B . . 109.5 ?
C5A C16A H16C . . 109.5 ?
H16A C16A H16C . . 109.5 ?
H16B C16A H16C . . 109.5 ?
C22A C17A C18A . . 117.4(2) ?
C22A C17A C6A . . 121.5(2) ?
C18A C17A C6A . . 120.81(19) ?
C19A C18A C17A . . 121.2(2) ?
C19A C18A H18A . . 119.4 ?
C17A C18A H18A . . 119.4 ?
C20A C19A C18A . . 120.2(2) ?
C20A C19A H19A . . 119.9 ?
C18A C19A H19A . . 119.9 ?
O4A C20A C21A . . 124.9(2) ?
O4A C20A C19A . . 115.7(2) ?
C21A C20A C19A . . 119.4(2) ?
C20A C21A C22A . . 119.7(2) ?
C20A C21A H21A . . 120.1 ?
C22A C21A H21A . . 120.1 ?
C17A C22A C21A . . 121.9(2) ?
C17A C22A H22A . . 119.1 ?
C21A C22A H22A . . 119.1 ?
O4A C23A H23A . . 109.5 ?
O4A C23A H23B . . 109.5 ?
H23A C23A H23B . . 109.5 ?
O4A C23A H23C . . 109.5 ?
H23A C23A H23C . . 109.5 ?
H23B C23A H23C . . 109.5 ?
C12B O2B C15B . . 118.1(2) ?
C20B O4B C23B . . 117.1(2) ?
C7B N1B C2B . . 116.88(17) ?
C7B N1B C6B . . 121.37(18) ?
C2B N1B C6B . . 119.69(17) ?
N1B C2B C9B . . 113.03(17) ?
N1B C2B C3B . . 107.54(19) ?
C9B C2B C3B . . 115.62(19) ?
N1B C2B H2B . . 106.7 ?
C9B C2B H2B . . 106.7 ?
C3B C2B H2B . . 106.7 ?
C4B C3B C2B . . 113.53(19) ?
C4B C3B H3C . . 108.9 ?
C2B C3B H3C . . 108.9 ?
C4B C3B H3D . . 108.9 ?
C2B C3B H3D . . 108.9 ?
H3C C3B H3D . . 107.7 ?
O3B C4B C3B . . 121.3(2) ?
O3B C4B C5B . . 122.0(2) ?
C3B C4B C5B . . 116.6(2) ?
C4B C5B C16B . . 112.1(2) ?
C4B C5B C6B . . 113.52(18) ?
C16B C5B C6B . . 111.3(2) ?
C4B C5B H5B . . 106.5 ?
C16B C5B H5B . . 106.5 ?
C6B C5B H5B . . 106.5 ?
N1B C6B C17B . . 112.70(17) ?
N1B C6B C5B . . 111.29(18) ?
C17B C6B C5B . . 108.99(17) ?
N1B C6B H6B . . 107.9 ?
C17B C6B H6B . . 107.9 ?
C5B C6B H6B . . 107.9 ?
O1B C7B N1B . . 122.5(2) ?
O1B C7B C8B . . 121.2(2) ?
N1B C7B C8B . . 116.25(19) ?
C7B C8B Cl1B . . 112.11(16) ?
C7B C8B H8C . . 109.2 ?
Cl1B C8B H8C . . 109.2 ?
C7B C8B H8D . . 109.2 ?
Cl1B C8B H8D . . 109.2 ?
H8C C8B H8D . . 107.9 ?
C14B C9B C10B . . 116.8(2) ?
C14B C9B C2B . . 123.9(2) ?
C10B C9B C2B . . 119.4(2) ?
C11B C10B C9B . . 121.8(2) ?
C11B C10B H10B . . 119.1 ?
C9B C10B H10B . . 119.1 ?
C12B C11B C10B . . 119.9(2) ?
C12B C11B H11B . . 120.0 ?
C10B C11B H11B . . 120.0 ?
O2B C12B C13B . . 124.1(2) ?
O2B C12B C11B . . 116.5(2) ?
C13B C12B C11B . . 119.4(2) ?
C12B C13B C14B . . 119.8(2) ?
C12B C13B H13B . . 120.1 ?
C14B C13B H13B . . 120.1 ?
C9B C14B C13B . . 122.2(2) ?
C9B C14B H14B . . 118.9 ?
C13B C14B H14B . . 118.9 ?
O2B C15B H15D . . 109.5 ?
O2B C15B H15E . . 109.5 ?
H15D C15B H15E . . 109.5 ?
O2B C15B H15F . . 109.5 ?
H15D C15B H15F . . 109.5 ?
H15E C15B H15F . . 109.5 ?
C5B C16B H16D . . 109.5 ?
C5B C16B H16E . . 109.5 ?
H16D C16B H16E . . 109.5 ?
C5B C16B H16F . . 109.5 ?
H16D C16B H16F . . 109.5 ?
H16E C16B H16F . . 109.5 ?
C18B C17B C22B . . 117.4(2) ?
C18B C17B C6B . . 120.8(2) ?
C22B C17B C6B . . 121.5(2) ?
C19B C18B C17B . . 121.9(2) ?
C19B C18B H18B . . 119.0 ?
C17B C18B H18B . . 119.0 ?
C18B C19B C20B . . 119.7(2) ?
C18B C19B H19B . . 120.2 ?
C20B C19B H19B . . 120.2 ?
O4B C20B C21B . . 124.4(2) ?
O4B C20B C19B . . 116.0(2) ?
C21B C20B C19B . . 119.6(2) ?
C20B C21B C22B . . 119.6(2) ?
C20B C21B H21B . . 120.2 ?
C22B C21B H21B . . 120.2 ?
C17B C22B C21B . . 121.7(2) ?
C17B C22B H22B . . 119.1 ?
C21B C22B H22B . . 119.1 ?
O4B C23B H23D . . 109.5 ?
O4B C23B H23E . . 109.5 ?
H23D C23B H23E . . 109.5 ?
O4B C23B H23F . . 109.5 ?
H23D C23B H23F . . 109.5 ?
H23E C23B H23F . . 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
Cl1A C8A . 1.762(2) ?
O1A C7A . 1.223(3) ?
O2A C12A . 1.375(3) ?
O2A C15A . 1.417(4) ?
O3A C4A . 1.205(3) ?
O4A C20A . 1.362(3) ?
O4A C23A . 1.420(3) ?
N1A C7A . 1.359(3) ?
N1A C2A . 1.477(3) ?
N1A C6A . 1.494(3) ?
C2A C3A . 1.517(3) ?
C2A C9A . 1.521(3) ?
C2A H2A . 0.9800 ?
C3A C4A . 1.499(3) ?
C3A H3A . 0.9700 ?
C3A H3B . 0.9700 ?
C4A C5A . 1.511(3) ?
C5A C16A . 1.521(3) ?
C5A C6A . 1.553(3) ?
C5A H5A . 0.9800 ?
C6A C17A . 1.514(3) ?
C6A H6A . 0.9800 ?
C7A C8A . 1.515(3) ?
C8A H8A . 0.9700 ?
C8A H8B . 0.9700 ?
C9A C14A . 1.380(3) ?
C9A C10A . 1.387(3) ?
C10A C11A . 1.378(4) ?
C10A H10A . 0.9300 ?
C11A C12A . 1.374(3) ?
C11A H11A . 0.9300 ?
C12A C13A . 1.369(3) ?
C13A C14A . 1.388(3) ?
C13A H13A . 0.9300 ?
C14A H14A . 0.9300 ?
C15A H15A . 0.9600 ?
C15A H15B . 0.9600 ?
C15A H15C . 0.9600 ?
C16A H16A . 0.9600 ?
C16A H16B . 0.9600 ?
C16A H16C . 0.9600 ?
C17A C22A . 1.379(3) ?
C17A C18A . 1.384(3) ?
C18A C19A . 1.383(3) ?
C18A H18A . 0.9300 ?
C19A C20A . 1.376(3) ?
C19A H19A . 0.9300 ?
C20A C21A . 1.373(3) ?
C21A C22A . 1.383(3) ?
C21A H21A . 0.9300 ?
C22A H22A . 0.9300 ?
C23A H23A . 0.9600 ?
C23A H23B . 0.9600 ?
C23A H23C . 0.9600 ?
Cl1B C8B . 1.768(2) ?
O1B C7B . 1.225(3) ?
O2B C12B . 1.372(3) ?
O2B C15B . 1.412(4) ?
O3B C4B . 1.215(3) ?
O4B C20B . 1.372(3) ?
O4B C23B . 1.408(4) ?
N1B C7B . 1.358(3) ?
N1B C2B . 1.476(3) ?
N1B C6B . 1.496(3) ?
C2B C9B . 1.520(3) ?
C2B C3B . 1.525(3) ?
C2B H2B . 0.9800 ?
C3B C4B . 1.486(3) ?
C3B H3C . 0.9700 ?
C3B H3D . 0.9700 ?
C4B C5B . 1.510(3) ?
C5B C16B . 1.516(3) ?
C5B C6B . 1.553(3) ?
C5B H5B . 0.9800 ?
C6B C17B . 1.518(3) ?
C6B H6B . 0.9800 ?
C7B C8B . 1.507(3) ?
C8B H8C . 0.9700 ?
C8B H8D . 0.9700 ?
C9B C14B . 1.376(3) ?
C9B C10B . 1.388(3) ?
C10B C11B . 1.382(4) ?
C10B H10B . 0.9300 ?
C11B C12B . 1.376(4) ?
C11B H11B . 0.9300 ?
C12B C13B . 1.375(3) ?
C13B C14B . 1.383(3) ?
C13B H13B . 0.9300 ?
C14B H14B . 0.9300 ?
C15B H15D . 0.9600 ?
C15B H15E . 0.9600 ?
C15B H15F . 0.9600 ?
C16B H16D . 0.9600 ?
C16B H16E . 0.9600 ?
C16B H16F . 0.9600 ?
C17B C18B . 1.379(3) ?
C17B C22B . 1.380(3) ?
C18B C19B . 1.378(3) ?
C18B H18B . 0.9300 ?
C19B C20B . 1.382(4) ?
C19B H19B . 0.9300 ?
C20B C21B . 1.375(3) ?
C21B C22B . 1.387(3) ?
C21B H21B . 0.9300 ?
C22B H22B . 0.9300 ?
C23B H23D . 0.9600 ?
C23B H23E . 0.9600 ?
C23B H23F . 0.9600 ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
C3A H3A O3B 1 0.97 2.58 3.063(3) 110.8
C6A H6A O1B 1_655 0.98 2.53 3.350(3) 141.7
C6B H6B O1A 1 0.98 2.54 3.363(3) 141.5
C8A H8B Cl1B 1_655 0.97 2.81 3.684(3) 149.6
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_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
C7A N1A C2A C3A . . . . -114.3(2) ?
C6A N1A C2A C3A . . . . 50.6(2) ?
C7A N1A C2A C9A . . . . 116.2(2) ?
C6A N1A C2A C9A . . . . -78.9(2) ?
N1A C2A C3A C4A . . . . -57.1(3) ?
C9A C2A C3A C4A . . . . 70.4(3) ?
C2A C3A C4A O3A . . . . -162.9(2) ?
C2A C3A C4A C5A . . . . 15.6(3) ?
O3A C4A C5A C16A . . . . -19.6(3) ?
C3A C4A C5A C16A . . . . 161.9(2) ?
O3A C4A C5A C6A . . . . -146.9(2) ?
C3A C4A C5A C6A . . . . 34.7(3) ?
C7A N1A C6A C17A . . . . -74.5(2) ?
C2A N1A C6A C17A . . . . 121.3(2) ?
C7A N1A C6A C5A . . . . 162.34(18) ?
C2A N1A C6A C5A . . . . -1.9(2) ?
C4A C5A C6A N1A . . . . -41.6(2) ?
C16A C5A C6A N1A . . . . -169.42(19) ?
C4A C5A C6A C17A . . . . -167.52(18) ?
C16A C5A C6A C17A . . . . 64.7(2) ?
C2A N1A C7A O1A . . . . -13.2(3) ?
C6A N1A C7A O1A . . . . -177.7(2) ?
C2A N1A C7A C8A . . . . 166.74(19) ?
C6A N1A C7A C8A . . . . 2.2(3) ?
O1A C7A C8A Cl1A . . . . 0.2(3) ?
N1A C7A C8A Cl1A . . . . -179.68(16) ?
N1A C2A C9A C14A . . . . 121.4(2) ?
C3A C2A C9A C14A . . . . -3.4(3) ?
N1A C2A C9A C10A . . . . -57.8(3) ?
C3A C2A C9A C10A . . . . 177.4(2) ?
C14A C9A C10A C11A . . . . -2.5(4) ?
C2A C9A C10A C11A . . . . 176.8(2) ?
C9A C10A C11A C12A . . . . 0.5(4) ?
C10A C11A C12A C13A . . . . 1.4(4) ?
C10A C11A C12A O2A . . . . -177.3(2) ?
C15A O2A C12A C13A . . . . -2.9(4) ?
C15A O2A C12A C11A . . . . 175.8(3) ?
C11A C12A C13A C14A . . . . -1.2(4) ?
O2A C12A C13A C14A . . . . 177.4(2) ?
C10A C9A C14A C13A . . . . 2.6(4) ?
C2A C9A C14A C13A . . . . -176.6(2) ?
C12A C13A C14A C9A . . . . -0.8(4) ?
N1A C6A C17A C22A . . . . -55.9(3) ?
C5A C6A C17A C22A . . . . 68.8(3) ?
N1A C6A C17A C18A . . . . 130.6(2) ?
C5A C6A C17A C18A . . . . -104.6(2) ?
C22A C17A C18A C19A . . . . -2.5(3) ?
C6A C17A C18A C19A . . . . 171.2(2) ?
C17A C18A C19A C20A . . . . -0.6(4) ?
C23A O4A C20A C21A . . . . -7.8(4) ?
C23A O4A C20A C19A . . . . 172.7(2) ?
C18A C19A C20A O4A . . . . -176.6(2) ?
C18A C19A C20A C21A . . . . 3.8(4) ?
O4A C20A C21A C22A . . . . 176.6(2) ?
C19A C20A C21A C22A . . . . -3.8(4) ?
C18A C17A C22A C21A . . . . 2.5(3) ?
C6A C17A C22A C21A . . . . -171.2(2) ?
C20A C21A C22A C17A . . . . 0.7(4) ?
C7B N1B C2B C9B . . . . -116.8(2) ?
C6B N1B C2B C9B . . . . 79.3(2) ?
C7B N1B C2B C3B . . . . 114.3(2) ?
C6B N1B C2B C3B . . . . -49.6(2) ?
N1B C2B C3B C4B . . . . 56.5(3) ?
C9B C2B C3B C4B . . . . -70.9(3) ?
C2B C3B C4B O3B . . . . 162.0(2) ?
C2B C3B C4B C5B . . . . -15.2(3) ?
O3B C4B C5B C16B . . . . 20.4(3) ?
C3B C4B C5B C16B . . . . -162.4(2) ?
O3B C4B C5B C6B . . . . 147.6(2) ?
C3B C4B C5B C6B . . . . -35.2(3) ?
C7B N1B C6B C17B . . . . 75.1(2) ?
C2B N1B C6B C17B . . . . -121.8(2) ?
C7B N1B C6B C5B . . . . -162.16(19) ?
C2B N1B C6B C5B . . . . 1.0(3) ?
C4B C5B C6B N1B . . . . 42.3(3) ?
C16B C5B C6B N1B . . . . 169.9(2) ?
C4B C5B C6B C17B . . . . 167.23(19) ?
C16B C5B C6B C17B . . . . -65.2(2) ?
C2B N1B C7B O1B . . . . 13.3(3) ?
C6B N1B C7B O1B . . . . 176.9(2) ?
C2B N1B C7B C8B . . . . -165.06(19) ?
C6B N1B C7B C8B . . . . -1.5(3) ?
O1B C7B C8B Cl1B . . . . 3.9(3) ?
N1B C7B C8B Cl1B . . . . -177.72(16) ?
N1B C2B C9B C14B . . . . -121.1(2) ?
C3B C2B C9B C14B . . . . 3.5(3) ?
N1B C2B C9B C10B . . . . 58.8(3) ?
C3B C2B C9B C10B . . . . -176.7(2) ?
C14B C9B C10B C11B . . . . 2.8(4) ?
C2B C9B C10B C11B . . . . -177.0(2) ?
C9B C10B C11B C12B . . . . -0.6(4) ?
C15B O2B C12B C13B . . . . 3.9(4) ?
C15B O2B C12B C11B . . . . -175.7(3) ?
C10B C11B C12B O2B . . . . 177.7(2) ?
C10B C11B C12B C13B . . . . -1.9(4) ?
O2B C12B C13B C14B . . . . -177.6(2) ?
C11B C12B C13B C14B . . . . 2.0(4) ?
C10B C9B C14B C13B . . . . -2.8(4) ?
C2B C9B C14B C13B . . . . 177.1(2) ?
C12B C13B C14B C9B . . . . 0.4(4) ?
N1B C6B C17B C18B . . . . -131.7(2) ?
C5B C6B C17B C18B . . . . 104.2(2) ?
N1B C6B C17B C22B . . . . 54.4(3) ?
C5B C6B C17B C22B . . . . -69.6(3) ?
C22B C17B C18B C19B . . . . 1.1(3) ?
C6B C17B C18B C19B . . . . -173.0(2) ?
C17B C18B C19B C20B . . . . 0.8(4) ?
C23B O4B C20B C21B . . . . 15.2(4) ?
C23B O4B C20B C19B . . . . -166.2(3) ?
C18B C19B C20B O4B . . . . 178.9(2) ?
C18B C19B C20B C21B . . . . -2.4(4) ?
O4B C20B C21B C22B . . . . -179.3(2) ?
C19B C20B C21B C22B . . . . 2.2(4) ?
C18B C17B C22B C21B . . . . -1.4(3) ?
C6B C17B C22B C21B . . . . 172.7(2) ?
C20B C21B C22B C17B . . . . -0.3(4) ?
