#------------------------------------------------------------------------------
#$Date: 2016-02-21 00:03:34 +0000 (Sun, 21 Feb 2016) $
#$Revision: 176798 $
#$URL: svn://www.crystallography.net/cod/cif/2/23/90/2239063.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_2239063
loop_
_publ_author_name
'Saidov, Abdusalom Sh.'
'Turgunov, Kambarali K.'
_publ_section_title
;
[2-(3,4-Dimethoxyphenyl)ethyl](3-{N-[2-(3,4-dimethoxyphenyl)ethyl]carbamoyl}propyl)azanium
chloride dihydrate
;
_journal_issue 2
_journal_name_full 'Acta Crystallographica Section E'
_journal_page_first o232
_journal_paper_doi 10.1107/S1600536814001998
_journal_volume 70
_journal_year 2014
_chemical_formula_iupac 'C24 H35 N2 O5 +, Cl -, 2H2 O'
_chemical_formula_moiety 'C24 H35 N2 O5 +, Cl -, 2(H2 O)'
_chemical_formula_sum 'C24 H39 Cl N2 O7'
_chemical_formula_weight 503.02
_chemical_melting_point 406(2)
_chemical_name_systematic
'[2-(3,4-Dimethoxyphenyl)ethyl](3-{N-[2-(3,4-dimethoxyphenyl)ethyl]carbamoyl}propyl)azanium chloride dihydrate'
_space_group_IT_number 14
_symmetry_cell_setting monoclinic
_symmetry_space_group_name_Hall '-P 2ybc'
_symmetry_space_group_name_H-M 'P 1 21/c 1'
_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 93.490(9)
_cell_angle_gamma 90.00
_cell_formula_units_Z 4
_cell_length_a 21.977(3)
_cell_length_b 12.2295(10)
_cell_length_c 10.2217(9)
_cell_measurement_reflns_used 3039
_cell_measurement_temperature 295(2)
_cell_measurement_theta_max 67.2386
_cell_measurement_theta_min 3.6071
_cell_volume 2742.2(5)
_computing_cell_refinement 'CrysAlis PRO (Oxford Diffraction, 2009)'
_computing_data_collection 'CrysAlis PRO (Oxford Diffraction, 2009)'
_computing_data_reduction 'CrysAlis PRO (Oxford Diffraction, 2009)'
_computing_molecular_graphics 'XP in SHELXTL (Sheldrick, 2008)'
_computing_publication_material 'publCIF (Westrip, 2010)'
_computing_structure_refinement 'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution 'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature 295(2)
_diffrn_detector_area_resol_mean 10.2576
_diffrn_measured_fraction_theta_full 0.988
_diffrn_measured_fraction_theta_max 0.988
_diffrn_measurement_device_type 'Oxford Diffraction Xcalibur Ruby'
_diffrn_measurement_method '\w scans'
_diffrn_radiation_monochromator graphite
_diffrn_radiation_source 'Enhance (Cu) X-ray Source'
_diffrn_radiation_type CuK\a
_diffrn_radiation_wavelength 1.54184
_diffrn_reflns_av_R_equivalents 0.0348
_diffrn_reflns_av_sigmaI/netI 0.0378
_diffrn_reflns_limit_h_max 26
_diffrn_reflns_limit_h_min -25
_diffrn_reflns_limit_k_max 12
_diffrn_reflns_limit_k_min -14
_diffrn_reflns_limit_l_max 12
_diffrn_reflns_limit_l_min -12
_diffrn_reflns_number 11225
_diffrn_reflns_theta_full 67.30
_diffrn_reflns_theta_max 67.30
_diffrn_reflns_theta_min 4.03
_exptl_absorpt_coefficient_mu 1.590
_exptl_absorpt_correction_T_max 1.00000
_exptl_absorpt_correction_T_min 0.59846
_exptl_absorpt_correction_type multi-scan
_exptl_absorpt_process_details
;
(CrysAlis PRO; Oxford Diffraction, 2009)
;
_exptl_crystal_colour colourless
_exptl_crystal_density_diffrn 1.218
_exptl_crystal_density_method 'not measured'
_exptl_crystal_description prism
_exptl_crystal_F_000 1080
_exptl_crystal_size_max 0.60
_exptl_crystal_size_mid 0.40
_exptl_crystal_size_min 0.35
_refine_diff_density_max 0.195
_refine_diff_density_min -0.236
_refine_ls_extinction_method none
_refine_ls_goodness_of_fit_ref 0.973
_refine_ls_hydrogen_treatment mixed
_refine_ls_matrix_type full
_refine_ls_number_parameters 339
_refine_ls_number_reflns 4860
_refine_ls_number_restraints 0
_refine_ls_restrained_S_all 0.973
_refine_ls_R_factor_all 0.0854
_refine_ls_R_factor_gt 0.0463
_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/[\s^2^(Fo^2^)+(0.0748P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme calc
_refine_ls_wR_factor_gt 0.1124
_refine_ls_wR_factor_ref 0.1314
_reflns_number_gt 3012
_reflns_number_total 4860
_reflns_threshold_expression I>2sigma(I)
_iucr_refine_instructions_details
;
TITL
CELL 1.54184 21.9775 12.2295 10.2217 90 93.49 90
ZERR 4 0.0025 0.001 0.0009 0 0.009 0
LATT 1
SYMM -X,0.5+Y,0.5-Z
SFAC C H N O CL
UNIT 96 156 8 28 4
acta
L.S. 4
BOND $H
FMAP 2
PLAN 20
WGHT 0.0748 0.0000
FVAR 2.91111
CL1 5 0.603157 0.540017 0.437297 11.00000 0.08677 0.04623 =
0.07033 0.00041 -0.00305 0.00166
O1 4 0.045530 0.607603 -0.007966 11.00000 0.05762 0.09058 =
0.06280 0.00161 -0.01853 -0.00204
O2 4 0.044335 0.621034 0.244133 11.00000 0.04525 0.09184 =
0.06676 -0.00318 0.00151 0.00447
O3 4 0.353065 0.872549 0.454581 11.00000 0.05857 0.04295 =
0.10205 0.00390 -0.02087 0.00014
O4 4 0.833146 1.015420 0.907853 11.00000 0.08557 0.04932 =
0.07451 -0.00663 -0.02301 0.00187
O5 4 0.890123 0.847941 1.010188 11.00000 0.05145 0.06985 =
0.06725 0.00521 -0.01529 -0.00081
N1 3 0.339893 0.691242 0.442305 11.00000 0.04382 0.04151 =
0.07813 0.00367 -0.01547 -0.00041
N2 3 0.593962 0.769712 0.569127 11.00000 0.03911 0.04518 =
0.05290 -0.00621 -0.00436 -0.00063
C1 1 0.210199 0.588723 0.214643 11.00000 0.04651 0.04352 =
0.05991 -0.00389 -0.00465 -0.00003
C2 1 0.210353 0.580542 0.080317 11.00000 0.05069 0.06618 =
0.05847 -0.00404 0.00515 -0.00257
AFIX 43
H2A 2 0.246942 0.571173 0.040537 11.00000 -1.20000
AFIX 0
C3 1 0.155773 0.586286 0.004001 11.00000 0.06522 0.07069 =
0.04506 -0.00099 -0.00026 -0.00809
AFIX 43
H3A 2 0.156491 0.580273 -0.086590 11.00000 -1.20000
AFIX 0
C4 1 0.101130 0.600551 0.058962 11.00000 0.05054 0.05074 =
0.05347 0.00298 -0.00744 -0.00608
C5 1 0.100497 0.608312 0.195968 11.00000 0.04548 0.04959 =
0.05375 -0.00454 -0.00183 0.00115
C6 1 0.154464 0.601526 0.270685 11.00000 0.04981 0.05514 =
0.04559 -0.00375 -0.00306 -0.00047
AFIX 43
H6A 2 0.153753 0.605606 0.361431 11.00000 -1.20000
AFIX 0
C7 1 0.043535 0.586182 -0.145775 11.00000 0.09163 0.10427 =
0.06165 -0.00104 -0.03252 -0.00842
AFIX 137
H7A 2 0.002000 0.588032 -0.180710 11.00000 -1.50000
H7B 2 0.060575 0.515323 -0.160747 11.00000 -1.50000
H7C 2 0.066690 0.640817 -0.188331 11.00000 -1.50000
AFIX 0
C8 1 0.039982 0.605911 0.381304 11.00000 0.07220 0.09547 =
0.07241 0.00107 0.02029 0.00491
AFIX 137
H8A 2 -0.002126 0.606281 0.401368 11.00000 -1.50000
H8B 2 0.061086 0.664092 0.427927 11.00000 -1.50000
H8C 2 0.058050 0.537159 0.407139 11.00000 -1.50000
AFIX 0
C9 1 0.268579 0.584268 0.300699 11.00000 0.04931 0.05015 =
0.07128 -0.01027 -0.00852 0.00251
AFIX 23
H9A 2 0.300309 0.550578 0.252471 11.00000 -1.20000
H9B 2 0.262317 0.539255 0.376850 11.00000 -1.20000
AFIX 0
C10 1 0.289093 0.697400 0.345311 11.00000 0.04401 0.04923 =
0.07204 0.00217 -0.01089 -0.00236
AFIX 23
H10A 2 0.301101 0.739090 0.270376 11.00000 -1.20000
H10B 2 0.255379 0.735207 0.382421 11.00000 -1.20000
AFIX 0
C11 1 0.368168 0.779958 0.491690 11.00000 0.03888 0.04657 =
0.06484 0.00002 -0.00077 -0.00131
C12 1 0.420556 0.760986 0.590509 11.00000 0.04208 0.04565 =
0.06524 -0.00368 -0.00561 -0.00100
AFIX 23
H12A 2 0.417376 0.688240 0.627288 11.00000 -1.20000
H12B 2 0.418539 0.813392 0.661346 11.00000 -1.20000
AFIX 0
C13 1 0.481569 0.772446 0.528309 11.00000 0.04166 0.05989 =
0.06057 -0.00615 -0.00511 0.00260
AFIX 23
H13A 2 0.486024 0.713501 0.466119 11.00000 -1.20000
H13B 2 0.482360 0.841030 0.480777 11.00000 -1.20000
AFIX 0
C14 1 0.534156 0.769407 0.630466 11.00000 0.03863 0.05480 =
0.06152 -0.00935 -0.00232 0.00276
AFIX 23
H14A 2 0.531853 0.832415 0.687592 11.00000 -1.20000
H14B 2 0.531080 0.704151 0.683601 11.00000 -1.20000
AFIX 0
C15 1 0.646809 0.774950 0.667174 11.00000 0.04112 0.06776 =
0.05401 -0.00351 -0.00926 -0.00334
AFIX 23
H15A 2 0.646704 0.710511 0.722489 11.00000 -1.20000
H15B 2 0.642511 0.838520 0.722608 11.00000 -1.20000
AFIX 0
C16 1 0.707331 0.781591 0.602986 11.00000 0.04534 0.07485 =
0.05956 -0.00551 -0.00359 -0.00381
AFIX 23
H16A 2 0.713871 0.715162 0.553926 11.00000 -1.20000
H16B 2 0.706819 0.842796 0.542571 11.00000 -1.20000
AFIX 0
C17 1 0.758000 0.796182 0.707410 11.00000 0.03706 0.06158 =
0.05644 -0.00138 -0.00104 -0.00284
C18 1 0.772075 0.900600 0.756152 11.00000 0.04509 0.05479 =
0.05407 0.00433 -0.00323 0.00524
AFIX 43
H18A 2 0.751273 0.960884 0.720524 11.00000 -1.20000
AFIX 0
C19 1 0.816145 0.915638 0.855852 11.00000 0.04813 0.04715 =
0.05494 0.00046 0.00057 -0.00114
C20 1 0.847367 0.825294 0.911720 11.00000 0.03642 0.05623 =
0.05436 0.00436 -0.00054 -0.00149
C21 1 0.833032 0.722904 0.863869 11.00000 0.04577 0.05096 =
0.08314 0.00887 -0.00635 0.00573
AFIX 43
H21A 2 0.853228 0.662133 0.899873 11.00000 -1.20000
AFIX 0
C22 1 0.789039 0.709134 0.763053 11.00000 0.04988 0.04902 =
0.08626 -0.00470 -0.00431 -0.00524
AFIX 43
H22A 2 0.780256 0.639022 0.732139 11.00000 -1.20000
AFIX 0
C23 1 0.798798 1.108087 0.864187 11.00000 0.12209 0.04987 =
0.06189 -0.00082 0.00176 0.01739
AFIX 137
H23A 2 0.814873 1.172292 0.907879 11.00000 -1.50000
H23B 2 0.756982 1.098398 0.883869 11.00000 -1.50000
H23C 2 0.801295 1.116281 0.771263 11.00000 -1.50000
AFIX 0
C24 1 0.919783 0.756844 1.073673 11.00000 0.05810 0.09669 =
0.07553 0.01915 -0.01556 0.01287
AFIX 137
H24A 2 0.948715 0.782606 1.140826 11.00000 -1.50000
H24B 2 0.940573 0.715041 1.010603 11.00000 -1.50000
H24C 2 0.890019 0.711590 1.112306 11.00000 -1.50000
AFIX 0
O1W 4 0.468012 0.511657 0.308458 11.00000 0.10359 0.09870 =
0.06981 0.01431 -0.01459 -0.02143
O2W 4 0.400727 1.049279 0.582653 11.00000 0.11432 0.05344 =
0.09481 0.01460 -0.03414 -0.01539
H1W2 2 0.384239 0.986925 0.536533 11.00000 0.15867
H2W2 2 0.423618 1.033883 0.643711 11.00000 0.11605
H1W1 2 0.448112 0.495185 0.375540 11.00000 0.15738
H2W1 2 0.509026 0.513412 0.329711 11.00000 0.16113
H1 2 0.351805 0.629490 0.475604 11.00000 0.05775
H2 2 0.597087 0.707092 0.519938 11.00000 0.07122
H3 2 0.595317 0.833775 0.510504 11.00000 0.06227
HKLF 4
REM
REM R1 = 0.0463 for 3012 Fo > 4sig(Fo) and 0.0854 for all 4860 data
REM 339 parameters refined using 0 restraints
END
;
_cod_data_source_file wm2799sup1.cif
_cod_data_source_block I
_cod_original_sg_symbol_H-M 'P 21/c'
_cod_database_code 2239063
_cod_database_fobs_code 2239063
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'
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_symmetry_multiplicity
Cl Cl1 0.60316(3) 0.54002(5) 0.43730(7) 0.0681(2) Uani d . 1 1
O O1 0.04553(8) 0.60760(16) -0.00797(18) 0.0712(5) Uani d . 1 1
O O2 0.04433(7) 0.62103(15) 0.24413(18) 0.0680(5) Uani d . 1 1
O O3 0.35306(8) 0.87255(13) 0.4546(2) 0.0689(5) Uani d . 1 1
O O4 0.83315(9) 1.01542(13) 0.90785(19) 0.0709(5) Uani d . 1 1
O O5 0.89012(7) 0.84794(15) 1.01019(17) 0.0636(5) Uani d . 1 1
N N1 0.33989(9) 0.69124(17) 0.4423(2) 0.0553(5) Uani d . 1 1
N N2 0.59396(8) 0.76971(17) 0.5691(2) 0.0460(5) Uani d . 1 1
C C1 0.21020(10) 0.58872(18) 0.2146(2) 0.0503(6) Uani d . 1 1
C C2 0.21035(11) 0.5805(2) 0.0803(2) 0.0584(6) Uani d . 1 1
H H2A 0.2469 0.5712 0.0405 0.070 Uiso calc R 1 1
C C3 0.15577(12) 0.5863(2) 0.0040(2) 0.0605(6) Uani d . 1 1
H H3A 0.1565 0.5803 -0.0866 0.073 Uiso calc R 1 1
C C4 0.10113(11) 0.60055(19) 0.0590(2) 0.0520(6) Uani d . 1 1
C C5 0.10050(10) 0.60831(18) 0.1960(2) 0.0498(6) Uani d . 1 1
C C6 0.15446(10) 0.60152(19) 0.2707(2) 0.0504(6) Uani d . 1 1
H H6A 0.1538 0.6056 0.3614 0.061 Uiso calc R 1 1
C C7 0.04354(15) 0.5862(3) -0.1458(3) 0.0874(10) Uani d . 1 1
H H7A 0.0020 0.5880 -0.1807 0.131 Uiso calc R 1 1
H H7B 0.0606 0.5153 -0.1608 0.131 Uiso calc R 1 1
H H7C 0.0667 0.6408 -0.1883 0.131 Uiso calc R 1 1
C C8 0.03998(14) 0.6059(3) 0.3813(3) 0.0794(9) Uani d . 1 1
H H8A -0.0021 0.6062 0.4014 0.119 Uiso calc R 1 1
H H8B 0.0611 0.6641 0.4279 0.119 Uiso calc R 1 1
H H8C 0.0581 0.5372 0.4072 0.119 Uiso calc R 1 1
C C9 0.26858(11) 0.58427(19) 0.3007(3) 0.0574(6) Uani d . 1 1
H H9A 0.3003 0.5506 0.2525 0.069 Uiso calc R 1 1
H H9B 0.2623 0.5393 0.3768 0.069 Uiso calc R 1 1
C C10 0.28909(10) 0.69740(19) 0.3453(3) 0.0557(6) Uani d . 1 1
H H10A 0.3011 0.7391 0.2704 0.067 Uiso calc R 1 1
H H10B 0.2554 0.7352 0.3824 0.067 Uiso calc R 1 1
C C11 0.36817(10) 0.77996(19) 0.4917(2) 0.0503(6) Uani d . 1 1
C C12 0.42055(10) 0.76099(19) 0.5905(3) 0.0514(6) Uani d . 1 1
H H12A 0.4174 0.6882 0.6273 0.062 Uiso calc R 1 1
H H12B 0.4185 0.8134 0.6613 0.062 Uiso calc R 1 1
C C13 0.48157(10) 0.7724(2) 0.5283(2) 0.0544(6) Uani d . 1 1
H H13A 0.4860 0.7135 0.4661 0.065 Uiso calc R 1 1
H H13B 0.4824 0.8410 0.4808 0.065 Uiso calc R 1 1
C C14 0.53415(10) 0.7694(2) 0.6305(2) 0.0519(6) Uani d . 1 1
H H14A 0.5319 0.8324 0.6876 0.062 Uiso calc R 1 1
H H14B 0.5311 0.7041 0.6836 0.062 Uiso calc R 1 1
C C15 0.64681(10) 0.7750(2) 0.6672(2) 0.0548(6) Uani d . 1 1
H H15A 0.6467 0.7105 0.7225 0.066 Uiso calc R 1 1
H H15B 0.6425 0.8385 0.7226 0.066 Uiso calc R 1 1
C C16 0.70733(10) 0.7816(2) 0.6030(3) 0.0602(7) Uani d . 1 1
H H16A 0.7139 0.7152 0.5539 0.072 Uiso calc R 1 1
H H16B 0.7068 0.8428 0.5426 0.072 Uiso calc R 1 1
C C17 0.75800(10) 0.7962(2) 0.7074(2) 0.0518(6) Uani d . 1 1
C C18 0.77208(10) 0.9006(2) 0.7562(2) 0.0516(6) Uani d . 1 1
H H18A 0.7513 0.9609 0.7205 0.062 Uiso calc R 1 1
C C19 0.81614(10) 0.91564(18) 0.8559(2) 0.0502(6) Uani d . 1 1
C C20 0.84737(10) 0.82529(19) 0.9117(2) 0.0491(6) Uani d . 1 1
C C21 0.83303(11) 0.72290(19) 0.8639(3) 0.0604(7) Uani d . 1 1
H H21A 0.8532 0.6621 0.8999 0.072 Uiso calc R 1 1
C C22 0.78904(11) 0.7091(2) 0.7631(3) 0.0621(7) Uani d . 1 1
H H22A 0.7803 0.6390 0.7321 0.074 Uiso calc R 1 1
C C23 0.79880(15) 1.1081(2) 0.8642(3) 0.0781(9) Uani d . 1 1
H H23A 0.8149 1.1723 0.9079 0.117 Uiso calc R 1 1
H H23B 0.7570 1.0984 0.8838 0.117 Uiso calc R 1 1
H H23C 0.8013 1.1163 0.7713 0.117 Uiso calc R 1 1
C C24 0.91979(13) 0.7568(2) 1.0737(3) 0.0776(9) Uani d . 1 1
H H24A 0.9487 0.7826 1.1408 0.116 Uiso calc R 1 1
H H24B 0.9406 0.7150 1.0106 0.116 Uiso calc R 1 1
H H24C 0.8900 0.7116 1.1123 0.116 Uiso calc R 1 1
O O1W 0.46801(16) 0.5117(2) 0.3085(3) 0.0915(7) Uani d . 1 1
O O2W 0.40073(12) 1.04928(17) 0.5826(3) 0.0892(8) Uani d . 1 1
H H1W2 0.3843(19) 0.987(4) 0.537(4) 0.159(17) Uiso d . 1 1
H H2W2 0.4236(18) 1.034(3) 0.644(4) 0.116(15) Uiso d . 1 1
H H1W1 0.448(2) 0.495(4) 0.376(5) 0.16(2) Uiso d . 1 1
H H2W1 0.509(2) 0.513(4) 0.330(4) 0.16(2) Uiso d . 1 1
H H1 0.3518(11) 0.629(2) 0.476(2) 0.058(7) Uiso d . 1 1
H H2 0.5971(11) 0.707(2) 0.520(3) 0.071(8) Uiso d . 1 1
H H3 0.5953(10) 0.834(2) 0.511(2) 0.062(7) Uiso d . 1 1
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_12
_atom_site_aniso_U_13
_atom_site_aniso_U_23
Cl1 0.0868(5) 0.0462(3) 0.0703(4) 0.0017(3) -0.0030(3) 0.0004(3)
O1 0.0576(11) 0.0906(14) 0.0628(11) -0.0020(10) -0.0185(9) 0.0016(10)
O2 0.0452(10) 0.0919(14) 0.0668(12) 0.0045(9) 0.0015(8) -0.0032(10)
O3 0.0586(11) 0.0429(10) 0.1020(15) 0.0001(8) -0.0209(10) 0.0039(9)
O4 0.0856(13) 0.0493(10) 0.0745(12) 0.0019(9) -0.0230(10) -0.0066(9)
O5 0.0515(10) 0.0699(11) 0.0673(11) -0.0008(8) -0.0153(8) 0.0052(9)
N1 0.0438(11) 0.0415(11) 0.0781(15) -0.0004(9) -0.0155(10) 0.0037(11)
N2 0.0391(11) 0.0452(11) 0.0529(12) -0.0006(8) -0.0044(9) -0.0062(10)
C1 0.0465(13) 0.0435(12) 0.0599(15) 0.0000(10) -0.0047(11) -0.0039(11)
C2 0.0507(14) 0.0662(16) 0.0585(16) -0.0026(12) 0.0052(12) -0.0041(13)
C3 0.0652(17) 0.0707(16) 0.0451(14) -0.0081(14) -0.0002(12) -0.0010(12)
C4 0.0505(14) 0.0507(14) 0.0535(15) -0.0061(11) -0.0074(11) 0.0030(11)
C5 0.0455(13) 0.0496(13) 0.0537(14) 0.0012(10) -0.0018(11) -0.0045(11)
C6 0.0498(13) 0.0551(14) 0.0456(13) -0.0004(11) -0.0031(11) -0.0037(11)
C7 0.092(2) 0.104(2) 0.0616(19) -0.0084(19) -0.0325(17) -0.0010(17)
C8 0.0722(19) 0.095(2) 0.072(2) 0.0049(16) 0.0203(15) 0.0011(17)
C9 0.0493(14) 0.0501(13) 0.0713(17) 0.0025(11) -0.0085(12) -0.0103(13)
C10 0.0440(13) 0.0493(14) 0.0720(17) -0.0024(11) -0.0109(12) 0.0022(12)
C11 0.0389(12) 0.0466(14) 0.0648(16) -0.0013(10) -0.0008(11) 0.0000(11)
C12 0.0421(13) 0.0456(13) 0.0652(16) -0.0010(10) -0.0056(11) -0.0037(11)
C13 0.0417(13) 0.0599(15) 0.0606(15) 0.0026(11) -0.0051(11) -0.0062(12)
C14 0.0386(12) 0.0548(14) 0.0615(15) 0.0028(10) -0.0023(11) -0.0094(11)
C15 0.0411(13) 0.0677(16) 0.0540(14) -0.0034(11) -0.0093(11) -0.0035(12)
C16 0.0453(14) 0.0749(18) 0.0596(15) -0.0038(12) -0.0036(12) -0.0055(13)
C17 0.0370(12) 0.0616(15) 0.0564(15) -0.0028(11) -0.0010(11) -0.0014(12)
C18 0.0451(13) 0.0548(14) 0.0541(14) 0.0052(11) -0.0032(11) 0.0044(11)
C19 0.0481(13) 0.0471(13) 0.0549(14) -0.0011(11) 0.0006(11) 0.0005(11)
C20 0.0364(12) 0.0562(14) 0.0544(14) -0.0015(10) -0.0005(11) 0.0044(11)
C21 0.0458(14) 0.0509(15) 0.0831(19) 0.0057(11) -0.0064(13) 0.0089(13)
C22 0.0499(14) 0.0490(14) 0.086(2) -0.0052(12) -0.0043(14) -0.0047(13)
C23 0.122(3) 0.0499(16) 0.0619(18) 0.0174(16) 0.0018(17) -0.0008(13)
C24 0.0581(17) 0.097(2) 0.076(2) 0.0129(15) -0.0156(15) 0.0192(17)
O1W 0.104(2) 0.0987(17) 0.0698(15) -0.0214(15) -0.0146(14) 0.0143(12)
O2W 0.1143(19) 0.0535(12) 0.0948(18) -0.0154(12) -0.0341(15) 0.0146(12)
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
C4 O1 C7 117.0(2)
C5 O2 C8 117.19(19)
C19 O4 C23 117.45(19)
C20 O5 C24 116.9(2)
C11 N1 C10 122.6(2)
C11 N1 H1 116.1(16)
C10 N1 H1 121.2(16)
C15 N2 C14 112.89(19)
C15 N2 H2 108.8(16)
C14 N2 H2 108.9(16)
C15 N2 H3 108.8(13)
C14 N2 H3 108.5(14)
H2 N2 H3 109(2)
C2 C1 C6 118.3(2)
C2 C1 C9 121.6(2)
C6 C1 C9 120.1(2)
C1 C2 C3 120.0(2)
C1 C2 H2A 120.0
C3 C2 H2A 120.0
C4 C3 C2 121.6(2)
C4 C3 H3A 119.2
C2 C3 H3A 119.2
O1 C4 C3 125.7(2)
O1 C4 C5 115.6(2)
C3 C4 C5 118.7(2)
O2 C5 C6 125.1(2)
O2 C5 C4 115.5(2)
C6 C5 C4 119.3(2)
C5 C6 C1 122.0(2)
C5 C6 H6A 119.0
C1 C6 H6A 119.0
O1 C7 H7A 109.5
O1 C7 H7B 109.5
H7A C7 H7B 109.5
O1 C7 H7C 109.5
H7A C7 H7C 109.5
H7B C7 H7C 109.5
O2 C8 H8A 109.5
O2 C8 H8B 109.5
H8A C8 H8B 109.5
O2 C8 H8C 109.5
H8A C8 H8C 109.5
H8B C8 H8C 109.5
C1 C9 C10 111.61(19)
C1 C9 H9A 109.3
C10 C9 H9A 109.3
C1 C9 H9B 109.3
C10 C9 H9B 109.3
H9A C9 H9B 108.0
N1 C10 C9 111.15(19)
N1 C10 H10A 109.4
C9 C10 H10A 109.4
N1 C10 H10B 109.4
C9 C10 H10B 109.4
H10A C10 H10B 108.0
O3 C11 N1 121.3(2)
O3 C11 C12 122.0(2)
N1 C11 C12 116.7(2)
C11 C12 C13 111.3(2)
C11 C12 H12A 109.4
C13 C12 H12A 109.4
C11 C12 H12B 109.4
C13 C12 H12B 109.4
H12A C12 H12B 108.0
C14 C13 C12 111.4(2)
C14 C13 H13A 109.3
C12 C13 H13A 109.3
C14 C13 H13B 109.3
C12 C13 H13B 109.3
H13A C13 H13B 108.0
N2 C14 C13 111.5(2)
N2 C14 H14A 109.3
C13 C14 H14A 109.3
N2 C14 H14B 109.3
C13 C14 H14B 109.3
H14A C14 H14B 108.0
N2 C15 C16 112.3(2)
N2 C15 H15A 109.2
C16 C15 H15A 109.2
N2 C15 H15B 109.2
C16 C15 H15B 109.2
H15A C15 H15B 107.9
C17 C16 C15 109.2(2)
C17 C16 H16A 109.8
C15 C16 H16A 109.8
C17 C16 H16B 109.8
C15 C16 H16B 109.8
H16A C16 H16B 108.3
C22 C17 C18 117.9(2)
C22 C17 C16 122.1(2)
C18 C17 C16 119.9(2)
C19 C18 C17 121.1(2)
C19 C18 H18A 119.4
C17 C18 H18A 119.4
O4 C19 C18 124.6(2)
O4 C19 C20 115.3(2)
C18 C19 C20 120.1(2)
O5 C20 C21 125.5(2)
O5 C20 C19 116.0(2)
C21 C20 C19 118.5(2)
C20 C21 C22 120.8(2)
C20 C21 H21A 119.6
C22 C21 H21A 119.6
C17 C22 C21 121.6(2)
C17 C22 H22A 119.2
C21 C22 H22A 119.2
O4 C23 H23A 109.5
O4 C23 H23B 109.5
H23A C23 H23B 109.5
O4 C23 H23C 109.5
H23A C23 H23C 109.5
H23B C23 H23C 109.5
O5 C24 H24A 109.5
O5 C24 H24B 109.5
H24A C24 H24B 109.5
O5 C24 H24C 109.5
H24A C24 H24C 109.5
H24B C24 H24C 109.5
H1W1 O1W H2W1 111(4)
H1W2 O2W H2W2 113(3)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O1 C4 1.366(3)
O1 C7 1.431(3)
O2 C5 1.365(3)
O2 C8 1.423(3)
O3 C11 1.233(3)
O4 C19 1.374(3)
O4 C23 1.419(3)
O5 C20 1.363(3)
O5 C24 1.427(3)
N1 C11 1.334(3)
N1 C10 1.449(3)
N1 H1 0.86(2)
N2 C15 1.488(3)
N2 C14 1.490(3)
N2 H2 0.92(3)
N2 H3 0.99(3)
C1 C2 1.377(3)
C1 C6 1.392(3)
C1 C9 1.512(3)
C2 C3 1.392(3)
C2 H2A 0.9300
C3 C4 1.368(3)
C3 H3A 0.9300
C4 C5 1.405(3)
C5 C6 1.373(3)
C6 H6A 0.9300
C7 H7A 0.9600
C7 H7B 0.9600
C7 H7C 0.9600
C8 H8A 0.9600
C8 H8B 0.9600
C8 H8C 0.9600
C9 C10 1.517(3)
C9 H9A 0.9700
C9 H9B 0.9700
C10 H10A 0.9700
C10 H10B 0.9700
C11 C12 1.503(3)
C12 C13 1.525(3)
C12 H12A 0.9700
C12 H12B 0.9700
C13 C14 1.510(3)
C13 H13A 0.9700
C13 H13B 0.9700
C14 H14A 0.9700
C14 H14B 0.9700
C15 C16 1.521(3)
C15 H15A 0.9700
C15 H15B 0.9700
C16 C17 1.505(3)
C16 H16A 0.9700
C16 H16B 0.9700
C17 C22 1.369(3)
C17 C18 1.398(3)
C18 C19 1.375(3)
C18 H18A 0.9300
C19 C20 1.404(3)
C20 C21 1.374(3)
C21 C22 1.380(3)
C21 H21A 0.9300
C22 H22A 0.9300
C23 H23A 0.9600
C23 H23B 0.9600
C23 H23C 0.9600
C24 H24A 0.9600
C24 H24B 0.9600
C24 H24C 0.9600
O1W H1W1 0.86(5)
O1W H2W1 0.91(5)
O2W H1W2 0.96(4)
O2W H2W2 0.80(4)
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
_geom_hbond_publ_flag
N1 H1 Cl1 3_666 0.87(2) 2.44(2) 3.300(2) 173(2) y
O2W H1W2 O3 1_555 0.95(5) 1.75(5) 2.704(3) 179(6) y
N2 H2 Cl1 1_555 0.92(3) 2.22(3) 3.127(2) 169(3) y
O2W H2W2 O1W 4_576 0.80(4) 1.97(4) 2.767(4) 171(4) y
N2 H3 O2W 3_676 0.99(2) 1.72(2) 2.709(3) 177(2) y
O1W H1W1 Cl1 3_666 0.87(5) 2.31(5) 3.177(3) 177(6) y
O1W H2W1 Cl1 1_555 0.91(4) 2.31(4) 3.194(4) 164(3) y