#------------------------------------------------------------------------------
#$Date: 2016-02-21 00:03:34 +0000 (Sun, 21 Feb 2016) $
#$Revision: 176798 $
#$URL: svn://www.crystallography.net/cod/cif/2/23/89/2238971.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_2238971
loop_
_publ_author_name
'Kavitha, Channappa N.'
'Kaur, Manpreet'
'Anderson, Brian J.'
'Jasinski, Jerry P.'
'Yathirajan, H. S.'
_publ_section_title
;
1-Piperonylpiperazinium picrate
;
_journal_coeditor_code SJ5385
_journal_issue 2
_journal_name_full 'Acta Crystallographica Section E'
_journal_page_first o208
_journal_page_last o209
_journal_paper_doi 10.1107/S1600536814001524
_journal_volume 70
_journal_year 2014
_chemical_formula_iupac 'C12 H17 N2 O2 +, C6 H2 N3 O7 -'
_chemical_formula_moiety 'C12 H17 N2 O2 +, C6 H2 N3 O7 -'
_chemical_formula_sum 'C18 H19 N5 O9'
_chemical_formula_weight 449.38
_chemical_name_common
;
1-Piperonylpiperazinium picrate
;
_chemical_name_systematic
;
4-(2H-1,3-Benzodioxol-5-ylmethyl)piperazin-1-ium
2,4,6-trinitrophenolate
;
_space_group_crystal_system monoclinic
_space_group_IT_number 14
_space_group_name_Hall '-P 2yn'
_space_group_name_H-M_alt 'P 1 21/n 1'
_symmetry_space_group_name_Hall '-P 2yn'
_symmetry_space_group_name_H-M 'P 1 21/n 1'
_atom_sites_solution_hydrogens mixed
_atom_sites_solution_primary direct
_audit_creation_method
;
Olex2 1.2
(compiled Apr 23 2013 17:54:37, GUI svn.r4466)
;
_cell_angle_alpha 90
_cell_angle_beta 96.5141(17)
_cell_angle_gamma 90
_cell_formula_units_Z 4
_cell_length_a 12.0864(2)
_cell_length_b 6.96981(11)
_cell_length_c 23.4898(4)
_cell_measurement_reflns_used 4971
_cell_measurement_temperature 173(2)
_cell_measurement_theta_max 72.3749
_cell_measurement_theta_min 3.6778
_cell_volume 1966.00(6)
_computing_cell_refinement 'CrysAlis PRO (Agilent, 2012)'
_computing_data_collection 'CrysAlis PRO (Agilent, 2012)'
_computing_data_reduction 'CrysAlis RED (Agilent, 2012)'
_computing_molecular_graphics 'OLEX2 (Dolomanov et al., 2009)'
_computing_publication_material 'OLEX2 (Dolomanov et al., 2009)'
_computing_structure_refinement 'SHELXL-2012 (Sheldrick, 2008)'
_computing_structure_solution 'SUPERFLIP (Palatinus & Chapuis, 2007)'
_diffrn_ambient_temperature 173(2)
_diffrn_detector_area_resol_mean 16.0416
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.984
_diffrn_measurement_device_type 'Agilent Gemini EOS'
_diffrn_measurement_method '\w scans'
_diffrn_radiation_type 'Cu K\a'
_diffrn_radiation_wavelength 1.5418
_diffrn_reflns_av_R_equivalents 0.0333
_diffrn_reflns_limit_h_max 14
_diffrn_reflns_limit_h_min -13
_diffrn_reflns_limit_k_max 8
_diffrn_reflns_limit_k_min -6
_diffrn_reflns_limit_l_max 28
_diffrn_reflns_limit_l_min -28
_diffrn_reflns_number 12154
_diffrn_reflns_theta_full 67.684
_diffrn_reflns_theta_max 72.525
_diffrn_reflns_theta_min 3.788
_exptl_absorpt_coefficient_mu 1.064
_exptl_absorpt_correction_T_max 1.00000
_exptl_absorpt_correction_T_min 0.76072
_exptl_absorpt_correction_type multi-scan
_exptl_absorpt_process_details
;
(CrysAlis PRO and CrysAlis RED; Agilent, 2012)
;
_exptl_crystal_colour 'dark yellow'
_exptl_crystal_density_diffrn 1.518
_exptl_crystal_description irregular
_exptl_crystal_F_000 936
_exptl_crystal_size_max 0.48
_exptl_crystal_size_mid 0.24
_exptl_crystal_size_min 0.22
_refine_diff_density_max 0.294
_refine_diff_density_min -0.209
_refine_ls_extinction_coef 0.0016(2)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method SHELXL
_refine_ls_goodness_of_fit_ref 1.050
_refine_ls_hydrogen_treatment mixed
_refine_ls_matrix_type full
_refine_ls_number_parameters 298
_refine_ls_number_reflns 3837
_refine_ls_number_restraints 0
_refine_ls_restrained_S_all 1.047
_refine_ls_R_factor_all 0.0481
_refine_ls_R_factor_gt 0.0425
_refine_ls_shift/su_max 0.000
_refine_ls_shift/su_mean 0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0679P)^2^+0.5476P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme calc
_refine_ls_wR_factor_gt 0.1153
_refine_ls_wR_factor_ref 0.1205
_reflns_number_gt 3316
_reflns_number_total 3837
_reflns_threshold_expression I>2\s(I)
_iucr_refine_instructions_details
;
TITL HSY-612 in P21/n
CELL 1.54184 12.086354 6.969806 23.48979 90 96.5141 90
ZERR 4 0.000205 0.000106 0.000431 0 0.0017 0
LATT 1
SYMM 0.5-X,0.5+Y,0.5-Z
SFAC C H N O
UNIT 72 76 20 36
EQIV $1 1-X,2-Y,1-Z
EQIV $2 1.5-X,-0.5+Y,0.5-Z
EQIV $3 -0.5+X,0.5-Y,-0.5+Z
EQIV $4 +X,1+Y,+Z
EQIV $5 0.5-X,-0.5+Y,0.5-Z
L.S. 15
PLAN 10
TEMP -100(2)
HTAB C3B O3B_$1
HTAB C4A O6B_$4
HTAB C10A O4B_$5
HTAB C10A O7B_$2
HTAB C11A O4B_$5
HTAB C11A O7B_$3
HTAB N2A O1B_$2
HTAB N2A O1B_$3
HTAB N2A O7B_$2
HTAB N2A O7B_$3
MORE -1
BOND $H
fmap 2
acta
CONF
OMIT -3 2 1
REM I:/Prof.Yathirajan%202013/HSY-612/HSY-612-MK/HSY-612.hkl
WGHT 0.067900 0.547600
EXTI 0.001590
FVAR 4.56598
O1B 4 0.845967 0.585132 0.471244 11.00000 0.02380 0.04690 =
0.03377 0.00200 -0.00141 -0.00221
O2B 4 0.775976 0.859941 0.538659 11.00000 0.05673 0.05628 =
0.05637 -0.01593 -0.01156 -0.01103
O3B 4 0.641005 1.016449 0.492235 11.00000 0.05601 0.03454 =
0.08078 -0.01075 0.00962 0.00348
O4B 4 0.329104 0.612893 0.423671 11.00000 0.02634 0.05052 =
0.06147 -0.00635 0.00228 0.00949
O5B 4 0.359188 0.346511 0.381170 11.00000 0.02815 0.04743 =
0.06196 -0.01327 0.00141 -0.00777
O6B 4 0.739474 0.156068 0.365610 11.00000 0.04292 0.05807 =
0.07732 -0.03517 0.00207 0.00813
O7B 4 0.856862 0.217441 0.439463 11.00000 0.03491 0.05714 =
0.07616 -0.00846 -0.00688 0.01914
N1B 3 0.695467 0.871032 0.502018 11.00000 0.03731 0.03530 =
0.03967 -0.00458 0.00693 -0.00638
N2B 3 0.392008 0.489442 0.408235 11.00000 0.02444 0.03876 =
0.03600 0.00245 0.00266 0.00110
N3B 3 0.768680 0.246866 0.409343 11.00000 0.02785 0.03456 =
0.04946 -0.00401 0.00555 0.00247
C1B 1 0.743258 0.560486 0.457160 11.00000 0.02434 0.03459 =
0.02272 0.00480 0.00070 -0.00004
C2B 1 0.660222 0.698410 0.469289 11.00000 0.02943 0.03004 =
0.02567 0.00106 0.00213 -0.00160
C3B 1 0.548346 0.678988 0.453103 11.00000 0.02757 0.03132 =
0.02731 0.00331 0.00513 0.00378
AFIX 43
H3B 2 0.497549 0.775456 0.462054 11.00000 -1.20000
AFIX 0
C4B 1 0.510807 0.515146 0.423315 11.00000 0.02283 0.03417 =
0.02594 0.00334 0.00152 0.00069
C5B 1 0.583196 0.375003 0.408674 11.00000 0.02752 0.03025 =
0.02690 -0.00035 0.00232 -0.00096
AFIX 43
H5B 2 0.556291 0.265124 0.387520 11.00000 -1.20000
AFIX 0
C6B 1 0.695163 0.398168 0.425428 11.00000 0.02584 0.03043 =
0.03035 0.00153 0.00352 0.00360
O1A 4 0.461813 0.971150 0.337546 11.00000 0.03199 0.03976 =
0.05278 -0.01527 0.00067 0.00167
O2A 4 0.316103 0.783062 0.296402 11.00000 0.02586 0.04809 =
0.06838 -0.02066 0.00133 0.00200
N1A 3 0.497955 0.222334 0.184794 11.00000 0.02555 0.03060 =
0.02715 -0.00143 -0.00076 -0.00098
N2A 3 0.451538 0.079260 0.070749 11.00000 0.02402 0.06416 =
0.03129 -0.01262 -0.00360 0.00382
C1A 1 0.571714 0.278872 0.235694 11.00000 0.02965 0.03509 =
0.03365 -0.00289 -0.00541 0.00285
AFIX 23
H1AA 2 0.649279 0.281604 0.225962 11.00000 -1.20000
H1AB 2 0.567628 0.180473 0.265779 11.00000 -1.20000
AFIX 0
C2A 1 0.544312 0.472213 0.259592 11.00000 0.02699 0.03282 =
0.02692 0.00043 -0.00151 -0.00137
C3A 1 0.630894 0.589771 0.282735 11.00000 0.02217 0.03657 =
0.03496 0.00030 0.00057 -0.00109
AFIX 43
H3A 2 0.705436 0.551381 0.279757 11.00000 -1.20000
AFIX 0
C4A 1 0.611907 0.762809 0.310277 11.00000 0.02514 0.03613 =
0.03339 -0.00133 -0.00192 -0.00625
AFIX 43
H4A 2 0.671382 0.841835 0.326453 11.00000 -1.20000
AFIX 0
C5A 1 0.502683 0.811816 0.312596 11.00000 0.03230 0.03057 =
0.02768 -0.00167 0.00152 -0.00208
C6A 1 0.343723 0.962913 0.323881 11.00000 0.03119 0.04494 =
0.06393 -0.01480 0.00245 0.00267
AFIX 23
H6AA 2 0.318076 1.070057 0.298018 11.00000 -1.20000
H6AB 2 0.306751 0.974118 0.359246 11.00000 -1.20000
AFIX 0
C7A 1 0.416076 0.699107 0.288193 11.00000 0.02278 0.03905 =
0.03354 -0.00028 0.00041 -0.00057
C8A 1 0.433083 0.527407 0.262076 11.00000 0.02439 0.03554 =
0.03334 -0.00400 -0.00325 -0.00430
AFIX 43
H8A 2 0.372652 0.449516 0.246419 11.00000 -1.20000
AFIX 0
C9A 1 0.517236 0.021565 0.171202 11.00000 0.03466 0.03135 =
0.03529 -0.00213 -0.00178 0.00123
AFIX 23
H9AA 2 0.507639 -0.059142 0.204975 11.00000 -1.20000
H9AB 2 0.594671 0.005638 0.162051 11.00000 -1.20000
AFIX 0
C10A 1 0.437101 -0.043872 0.120781 11.00000 0.03158 0.04319 =
0.04511 -0.01124 -0.00011 -0.00398
AFIX 23
H10A 2 0.452078 -0.179434 0.111669 11.00000 -1.20000
H10B 2 0.359592 -0.034311 0.130335 11.00000 -1.20000
AFIX 0
C11A 1 0.436050 0.285907 0.083848 11.00000 0.04217 0.05561 =
0.03321 0.00439 -0.00092 0.01142
AFIX 23
H11A 2 0.358410 0.308941 0.091735 11.00000 -1.20000
H11B 2 0.450534 0.365286 0.050537 11.00000 -1.20000
AFIX 0
C12A 1 0.515921 0.341083 0.135674 11.00000 0.03794 0.03552 =
0.03299 0.00234 0.00288 0.00064
AFIX 23
H12A 2 0.593501 0.325120 0.126752 11.00000 -1.20000
H12B 2 0.504883 0.477707 0.145083 11.00000 -1.20000
AFIX 0
H2AA 2 0.522142 0.062475 0.062253 11.00000 0.05276
H2AB 2 0.402502 0.044065 0.040283 11.00000 0.05596
HKLF 4
REM HSY-612 in P21/n
REM R1 = 0.0425 for 3316 Fo > 4sig(Fo) and 0.0481 for all 3837 data
REM 298 parameters refined using 0 restraints
END
WGHT 0.0669 0.5530
REM Highest difference peak 0.294, deepest hole -0.210, 1-sigma level 0.048
Q1 1 0.7305 0.0819 0.3969 11.00000 0.05 0.29
Q2 1 0.7859 0.9226 0.4996 11.00000 0.05 0.27
Q3 1 0.7000 0.6260 0.4686 11.00000 0.05 0.27
Q4 1 0.6220 0.9414 0.5234 11.00000 0.05 0.27
Q5 1 0.4650 0.7535 0.2913 11.00000 0.05 0.26
Q6 1 0.5832 0.5184 0.2779 11.00000 0.05 0.25
Q7 1 0.4926 0.4996 0.2604 11.00000 0.05 0.23
Q8 1 0.7189 0.4744 0.4342 11.00000 0.05 0.23
Q9 1 0.8668 0.2698 0.4036 11.00000 0.05 0.22
Q10 1 0.4240 0.5959 0.2915 11.00000 0.05 0.22
;
_cod_data_source_file sj5385sup1.cif
_cod_data_source_block I
_cod_original_cell_volume 1965.99(6)
_cod_database_code 2238971
_cod_database_fobs_code 2238971
#BEGIN Tags that were not found in dictionaries:
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_shelx_hkl_checksum 45740
_shelx_res_checksum 19714
#END Tags that were not found in dictionaries
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -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_occupancy
O O1B 0.84597(9) 0.58513(17) 0.47124(5) 0.0352(3) Uani d 1
O O2B 0.77598(13) 0.8599(2) 0.53866(6) 0.0578(4) Uani d 1
O O3B 0.64101(13) 1.01645(19) 0.49224(7) 0.0570(4) Uani d 1
O O4B 0.32910(10) 0.61289(19) 0.42367(6) 0.0463(3) Uani d 1
O O5B 0.35919(10) 0.34651(18) 0.38117(6) 0.0461(3) Uani d 1
O O6B 0.73947(12) 0.1561(2) 0.36561(7) 0.0598(4) Uani d 1
O O7B 0.85686(11) 0.2174(2) 0.43946(7) 0.0571(4) Uani d 1
N N1B 0.69547(12) 0.8710(2) 0.50202(6) 0.0372(3) Uani d 1
N N2B 0.39201(11) 0.4894(2) 0.40823(6) 0.0331(3) Uani d 1
N N3B 0.76868(11) 0.2469(2) 0.40934(6) 0.0372(3) Uani d 1
C C1B 0.74326(12) 0.5605(2) 0.45716(6) 0.0274(3) Uani d 1
C C2B 0.66022(13) 0.6984(2) 0.46929(6) 0.0285(3) Uani d 1
C C3B 0.54835(13) 0.6790(2) 0.45310(6) 0.0286(3) Uani d 1
H H3B 0.4975 0.7755 0.4621 0.034 Uiso calc 1
C C4B 0.51081(12) 0.5151(2) 0.42331(6) 0.0277(3) Uani d 1
C C5B 0.58320(13) 0.3750(2) 0.40867(6) 0.0283(3) Uani d 1
H H5B 0.5563 0.2651 0.3875 0.034 Uiso calc 1
C C6B 0.69516(12) 0.3982(2) 0.42543(6) 0.0288(3) Uani d 1
O O1A 0.46181(10) 0.97115(18) 0.33755(6) 0.0418(3) Uani d 1
O O2A 0.31610(10) 0.78306(19) 0.29640(6) 0.0478(3) Uani d 1
N N1A 0.49795(10) 0.22233(18) 0.18479(5) 0.0281(3) Uani d 1
N N2A 0.45154(12) 0.0793(2) 0.07075(6) 0.0403(4) Uani d 1
C C1A 0.57171(13) 0.2789(2) 0.23569(7) 0.0335(4) Uani d 1
H H1AA 0.6493 0.2816 0.2260 0.040 Uiso calc 1
H H1AB 0.5676 0.1805 0.2658 0.040 Uiso calc 1
C C2A 0.54431(13) 0.4722(2) 0.25959(6) 0.0293(3) Uani d 1
C C3A 0.63089(12) 0.5898(2) 0.28273(7) 0.0314(3) Uani d 1
H H3A 0.7054 0.5514 0.2798 0.038 Uiso calc 1
C C4A 0.61191(13) 0.7628(2) 0.31028(7) 0.0320(3) Uani d 1
H H4A 0.6714 0.8418 0.3265 0.038 Uiso calc 1
C C5A 0.50268(13) 0.8118(2) 0.31260(6) 0.0303(3) Uani d 1
C C6A 0.34372(15) 0.9629(3) 0.32388(9) 0.0469(5) Uani d 1
H H6AA 0.3181 1.0701 0.2980 0.056 Uiso calc 1
H H6AB 0.3068 0.9741 0.3592 0.056 Uiso calc 1
C C7A 0.41608(13) 0.6991(2) 0.28819(7) 0.0320(3) Uani d 1
C C8A 0.43308(13) 0.5274(2) 0.26208(7) 0.0316(3) Uani d 1
H H8A 0.3727 0.4495 0.2464 0.038 Uiso calc 1
C C9A 0.51724(14) 0.0216(2) 0.17120(7) 0.0342(4) Uani d 1
H H9AA 0.5076 -0.0591 0.2050 0.041 Uiso calc 1
H H9AB 0.5947 0.0056 0.1621 0.041 Uiso calc 1
C C10A 0.43710(14) -0.0439(3) 0.12078(8) 0.0403(4) Uani d 1
H H10A 0.4521 -0.1794 0.1117 0.048 Uiso calc 1
H H10B 0.3596 -0.0343 0.1303 0.048 Uiso calc 1
C C11A 0.43605(16) 0.2859(3) 0.08385(8) 0.0441(4) Uani d 1
H H11A 0.3584 0.3089 0.0917 0.053 Uiso calc 1
H H11B 0.4505 0.3653 0.0505 0.053 Uiso calc 1
C C12A 0.51592(14) 0.3411(2) 0.13567(7) 0.0356(4) Uani d 1
H H12A 0.5935 0.3251 0.1268 0.043 Uiso calc 1
H H12B 0.5049 0.4777 0.1451 0.043 Uiso calc 1
H H2AA 0.522(2) 0.062(3) 0.0623(9) 0.053(6) Uiso d 1
H H2AB 0.403(2) 0.044(3) 0.0403(10) 0.056(6) Uiso d 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
O1B 0.0238(6) 0.0469(7) 0.0338(6) -0.0022(5) -0.0014(4) 0.0020(5)
O2B 0.0567(9) 0.0563(9) 0.0564(9) -0.0110(7) -0.0116(7) -0.0159(7)
O3B 0.0560(9) 0.0345(7) 0.0808(11) 0.0035(6) 0.0096(7) -0.0108(7)
O4B 0.0263(6) 0.0505(8) 0.0615(8) 0.0095(5) 0.0023(5) -0.0064(6)
O5B 0.0281(6) 0.0474(7) 0.0620(8) -0.0078(5) 0.0014(5) -0.0133(6)
O6B 0.0429(8) 0.0581(9) 0.0773(10) 0.0081(6) 0.0021(7) -0.0352(8)
O7B 0.0349(7) 0.0571(9) 0.0762(10) 0.0191(6) -0.0069(7) -0.0085(7)
N1B 0.0373(8) 0.0353(8) 0.0397(8) -0.0064(6) 0.0069(6) -0.0046(6)
N2B 0.0244(7) 0.0388(7) 0.0360(7) 0.0011(5) 0.0027(5) 0.0025(6)
N3B 0.0278(7) 0.0346(7) 0.0495(9) 0.0025(6) 0.0055(6) -0.0040(6)
C1B 0.0243(7) 0.0346(8) 0.0227(7) 0.0000(6) 0.0007(5) 0.0048(6)
C2B 0.0294(8) 0.0300(8) 0.0257(7) -0.0016(6) 0.0021(6) 0.0011(6)
C3B 0.0276(8) 0.0313(7) 0.0273(7) 0.0038(6) 0.0051(6) 0.0033(6)
C4B 0.0228(7) 0.0342(8) 0.0259(7) 0.0007(6) 0.0015(6) 0.0033(6)
C5B 0.0275(8) 0.0303(7) 0.0269(7) -0.0010(6) 0.0023(6) -0.0003(6)
C6B 0.0258(8) 0.0304(8) 0.0304(7) 0.0036(6) 0.0035(6) 0.0015(6)
O1A 0.0320(6) 0.0398(7) 0.0528(8) 0.0017(5) 0.0007(5) -0.0153(5)
O2A 0.0259(6) 0.0481(7) 0.0684(9) 0.0020(5) 0.0013(6) -0.0207(6)
N1A 0.0256(6) 0.0306(6) 0.0271(6) -0.0010(5) -0.0008(5) -0.0014(5)
N2A 0.0240(7) 0.0642(10) 0.0313(7) 0.0038(6) -0.0036(6) -0.0126(7)
C1A 0.0297(8) 0.0351(8) 0.0336(8) 0.0028(6) -0.0054(6) -0.0029(6)
C2A 0.0270(8) 0.0328(8) 0.0269(7) -0.0014(6) -0.0015(6) 0.0004(6)
C3A 0.0222(7) 0.0366(8) 0.0350(8) -0.0011(6) 0.0006(6) 0.0003(6)
C4A 0.0251(8) 0.0361(8) 0.0334(8) -0.0062(6) -0.0019(6) -0.0013(6)
C5A 0.0323(8) 0.0306(8) 0.0277(7) -0.0021(6) 0.0015(6) -0.0017(6)
C6A 0.0312(9) 0.0449(10) 0.0639(12) 0.0027(7) 0.0025(8) -0.0148(9)
C7A 0.0228(7) 0.0391(8) 0.0335(8) -0.0006(6) 0.0004(6) -0.0003(6)
C8A 0.0244(7) 0.0355(8) 0.0333(8) -0.0043(6) -0.0032(6) -0.0040(6)
C9A 0.0347(8) 0.0313(8) 0.0353(8) 0.0012(6) -0.0018(7) -0.0021(6)
C10A 0.0316(9) 0.0432(9) 0.0451(10) -0.0040(7) -0.0001(7) -0.0112(8)
C11A 0.0422(10) 0.0556(11) 0.0332(9) 0.0114(8) -0.0009(7) 0.0044(8)
C12A 0.0379(9) 0.0355(8) 0.0330(8) 0.0006(7) 0.0029(7) 0.0023(6)
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'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
O2B N1B C2B 118.49(14)
O3B N1B O2B 123.68(15)
O3B N1B C2B 117.80(14)
O4B N2B C4B 118.01(14)
O5B N2B O4B 123.24(14)
O5B N2B C4B 118.76(13)
O6B N3B O7B 123.10(15)
O6B N3B C6B 117.76(14)
O7B N3B C6B 119.13(14)
O1B C1B C2B 123.00(14)
O1B C1B C6B 124.81(14)
C6B C1B C2B 112.14(13)
C1B C2B N1B 118.95(13)
C3B C2B N1B 116.50(13)
C3B C2B C1B 124.54(14)
C2B C3B H3B 120.7
C2B C3B C4B 118.51(14)
C4B C3B H3B 120.7
C3B C4B N2B 118.85(13)
C5B C4B N2B 119.31(14)
C5B C4B C3B 121.83(14)
C4B C5B H5B 120.8
C6B C5B C4B 118.45(14)
C6B C5B H5B 120.8
C1B C6B N3B 118.73(13)
C5B C6B N3B 116.76(13)
C5B C6B C1B 124.50(14)
C5A O1A C6A 105.68(12)
C7A O2A C6A 105.78(12)
C9A N1A C1A 109.85(12)
C12A N1A C1A 111.28(13)
C12A N1A C9A 109.25(12)
C10A N2A C11A 111.56(14)
C10A N2A H2AA 107.4(14)
C10A N2A H2AB 110.1(15)
C11A N2A H2AA 108.3(14)
C11A N2A H2AB 109.7(15)
H2AA N2A H2AB 110(2)
N1A C1A H1AA 108.8
N1A C1A H1AB 108.8
N1A C1A C2A 113.90(13)
H1AA C1A H1AB 107.7
C2A C1A H1AA 108.8
C2A C1A H1AB 108.8
C3A C2A C1A 118.94(14)
C3A C2A C8A 120.22(15)
C8A C2A C1A 120.69(14)
C2A C3A H3A 118.9
C2A C3A C4A 122.20(14)
C4A C3A H3A 118.9
C3A C4A H4A 121.9
C5A C4A C3A 116.24(14)
C5A C4A H4A 121.9
O1A C5A C7A 110.17(14)
C4A C5A O1A 127.81(14)
C4A C5A C7A 122.01(15)
O1A C6A O2A 108.21(13)
O1A C6A H6AA 110.1
O1A C6A H6AB 110.1
O2A C6A H6AA 110.1
O2A C6A H6AB 110.1
H6AA C6A H6AB 108.4
O2A C7A C5A 109.66(14)
C8A C7A O2A 127.79(14)
C8A C7A C5A 122.51(15)
C2A C8A H8A 121.6
C7A C8A C2A 116.75(14)
C7A C8A H8A 121.6
N1A C9A H9AA 109.5
N1A C9A H9AB 109.5
N1A C9A C10A 110.87(13)
H9AA C9A H9AB 108.1
C10A C9A H9AA 109.5
C10A C9A H9AB 109.5
N2A C10A C9A 108.90(14)
N2A C10A H10A 109.9
N2A C10A H10B 109.9
C9A C10A H10A 109.9
C9A C10A H10B 109.9
H10A C10A H10B 108.3
N2A C11A H11A 109.9
N2A C11A H11B 109.9
N2A C11A C12A 109.15(14)
H11A C11A H11B 108.3
C12A C11A H11A 109.9
C12A C11A H11B 109.9
N1A C12A C11A 110.72(14)
N1A C12A H12A 109.5
N1A C12A H12B 109.5
C11A C12A H12A 109.5
C11A C12A H12B 109.5
H12A C12A H12B 108.1
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O1B C1B 1.2597(18)
O2B N1B 1.226(2)
O3B N1B 1.216(2)
O4B N2B 1.2298(18)
O5B N2B 1.2234(18)
O6B N3B 1.2240(19)
O7B N3B 1.2278(18)
N1B C2B 1.465(2)
N2B C4B 1.4505(19)
N3B C6B 1.456(2)
C1B C2B 1.441(2)
C1B C6B 1.441(2)
C2B C3B 1.369(2)
C3B H3B 0.9500
C3B C4B 1.388(2)
C4B C5B 1.381(2)
C5B H5B 0.9500
C5B C6B 1.375(2)
O1A C5A 1.3735(19)
O1A C6A 1.428(2)
O2A C6A 1.432(2)
O2A C7A 1.3757(19)
N1A C1A 1.4621(19)
N1A C9A 1.460(2)
N1A C12A 1.456(2)
N2A C10A 1.481(2)
N2A C11A 1.489(2)
N2A H2AA 0.91(2)
N2A H2AB 0.91(2)
C1A H1AA 0.9900
C1A H1AB 0.9900
C1A C2A 1.511(2)
C2A C3A 1.390(2)
C2A C8A 1.406(2)
C3A H3A 0.9500
C3A C4A 1.400(2)
C4A H4A 0.9500
C4A C5A 1.371(2)
C5A C7A 1.380(2)
C6A H6AA 0.9900
C6A H6AB 0.9900
C7A C8A 1.371(2)
C8A H8A 0.9500
C9A H9AA 0.9900
C9A H9AB 0.9900
C9A C10A 1.513(2)
C10A H10A 0.9900
C10A H10B 0.9900
C11A H11A 0.9900
C11A H11B 0.9900
C11A C12A 1.515(2)
C12A H12A 0.9900
C12A H12B 0.9900
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
N2A H2AA O1B 2_645 0.91(2) 1.86(3) 2.7409(19) 163(2)
N2A H2AB O1B 4_565 0.91(2) 1.91(2) 2.7798(18) 159(2)
C4A H4A O6B 1_565 0.95 2.48 3.335(2) 149.8
C3B H3B O3B 3_676 0.95 2.54 3.473(2) 165.9
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
O1B C1B C2B N1B -3.2(2)
O1B C1B C2B C3B 177.92(14)
O1B C1B C6B N3B 1.8(2)
O1B C1B C6B C5B -177.91(14)
O2B N1B C2B C1B -32.4(2)
O2B N1B C2B C3B 146.50(16)
O3B N1B C2B C1B 149.48(15)
O3B N1B C2B C3B -31.6(2)
O4B N2B C4B C3B -1.5(2)
O4B N2B C4B C5B 177.30(14)
O5B N2B C4B C3B 178.82(14)
O5B N2B C4B C5B -2.4(2)
O6B N3B C6B C1B -150.82(16)
O6B N3B C6B C5B 28.9(2)
O7B N3B C6B C1B 28.4(2)
O7B N3B C6B C5B -151.86(16)
N1B C2B C3B C4B -178.32(13)
N2B C4B C5B C6B -177.33(13)
C1B C2B C3B C4B 0.6(2)
C2B C1B C6B N3B 179.38(13)
C2B C1B C6B C5B -0.4(2)
C2B C3B C4B N2B 177.29(13)
C2B C3B C4B C5B -1.5(2)
C3B C4B C5B C6B 1.4(2)
C4B C5B C6B N3B 179.77(13)
C4B C5B C6B C1B -0.5(2)
C6B C1B C2B N1B 179.19(13)
C6B C1B C2B C3B 0.3(2)
O1A C5A C7A O2A 0.31(19)
O1A C5A C7A C8A -177.63(15)
O2A C7A C8A C2A -179.39(16)
N1A C1A C2A C3A -143.67(15)
N1A C1A C2A C8A 40.7(2)
N1A C9A C10A N2A 58.56(18)
N2A C11A C12A N1A -57.98(19)
C1A N1A C9A C10A 176.60(14)
C1A N1A C12A C11A -177.88(14)
C1A C2A C3A C4A -174.11(15)
C1A C2A C8A C7A 175.38(14)
C2A C3A C4A C5A -0.8(2)
C3A C2A C8A C7A -0.2(2)
C3A C4A C5A O1A 179.11(15)
C3A C4A C5A C7A -1.2(2)
C4A C5A C7A O2A -179.39(15)
C4A C5A C7A C8A 2.7(3)
C5A O1A C6A O2A 7.0(2)
C5A C7A C8A C2A -1.8(2)
C6A O1A C5A C4A 175.15(17)
C6A O1A C5A C7A -4.53(19)
C6A O2A C7A C5A 4.0(2)
C6A O2A C7A C8A -178.15(17)
C7A O2A C6A O1A -6.8(2)
C8A C2A C3A C4A 1.6(2)
C9A N1A C1A C2A -169.57(13)
C9A N1A C12A C11A 60.66(17)
C10A N2A C11A C12A 56.16(19)
C11A N2A C10A C9A -56.31(18)
C12A N1A C1A C2A 69.32(17)
C12A N1A C9A C10A -61.07(17)