#------------------------------------------------------------------------------
#$Date: 2024-12-06 22:37:49 +0200 (Fri, 06 Dec 2024) $
#$Revision: 296690 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/16/01/7160188.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_7160188
loop_
_publ_author_name
'Zhang, Xinqin'
'Yang, Qin'
'Zeng, Xiaofeng'
'Fu, Yang'
'Ding, Qiuping'
'Peng, Yiyuan'
_publ_section_title
;
Highly selective synthesis of selenium-containing
(E)-N-propenolquinazolinones via
FeCl3-mediated cascade reaction of propargyl quinazoline-4-yl
ethers with diselenides.
;
_journal_issue 47
_journal_name_full 'Organic & biomolecular chemistry'
_journal_page_first 9231
_journal_page_last 9241
_journal_paper_doi 10.1039/d4ob01498g
_journal_volume 22
_journal_year 2024
_chemical_formula_moiety '0.33(C32 H28 N2 O2 Se)'
_chemical_formula_sum 'C10.67 H9.33 N0.67 O0.67 Se0.33'
_chemical_formula_weight 183.84
_space_group_crystal_system orthorhombic
_space_group_IT_number 19
_space_group_name_Hall 'P 2ac 2ab'
_space_group_name_H-M_alt 'P 21 21 21'
_atom_sites_solution_hydrogens geom
_atom_sites_solution_primary iterative
_audit_creation_date 2023-12-28
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2023-12-29 deposited with the CCDC. 2024-10-16 downloaded from the CCDC.
;
_cell_angle_alpha 90
_cell_angle_beta 90
_cell_angle_gamma 90
_cell_formula_units_Z 12
_cell_length_a 12.5627(11)
_cell_length_b 14.7048(7)
_cell_length_c 14.8441(7)
_cell_measurement_reflns_used 5278
_cell_measurement_temperature 293(2)
_cell_measurement_theta_max 23.4710
_cell_measurement_theta_min 3.8940
_cell_volume 2742.2(3)
_computing_cell_refinement 'CrysAlisPro 1.171.42.90a (Rigaku OD, 2023)'
_computing_data_collection 'CrysAlisPro 1.171.42.90a (Rigaku OD, 2023)'
_computing_data_reduction 'CrysAlisPro 1.171.42.90a (Rigaku OD, 2023)'
_computing_molecular_graphics 'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material 'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement 'ShelXL (Sheldrick, 2015)'
_computing_structure_solution 'olex2.solve (Bourhis et al., 2015)'
_diffrn_ambient_temperature 293(2)
_diffrn_detector 'CCD plate'
_diffrn_detector_area_resol_mean 16.0706
_diffrn_detector_type EosS2
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.875
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):
# Type Start End Width t~exp~ \w \q \k \f Frames
#--------------------------------------------------------------------------
1 \w -10.00 42.00 1.00 19.66 -- 16.70 77.00 -90.00 52
2 \w -15.00 55.00 1.00 19.66 -- 16.70 -99.00 90.00 70
3 \w -3.00 86.00 1.00 19.66 -- 16.70 37.00 150.00 89
4 \w -45.00 16.00 1.00 19.66 -- -15.76 19.00-120.00 61
;
_diffrn_measurement_device 'four-circle diffractometer'
_diffrn_measurement_device_type 'SuperNova, Single source at offset/far, EosS2'
_diffrn_measurement_method '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11 -0.0337244000
_diffrn_orient_matrix_UB_12 0.0306929000
_diffrn_orient_matrix_UB_13 0.0232195000
_diffrn_orient_matrix_UB_21 -0.0410264000
_diffrn_orient_matrix_UB_22 -0.0331562000
_diffrn_orient_matrix_UB_23 0.0002743000
_diffrn_orient_matrix_UB_31 0.0191048000
_diffrn_orient_matrix_UB_32 -0.0169090000
_diffrn_orient_matrix_UB_33 0.0417749000
_diffrn_radiation_monochromator mirror
_diffrn_radiation_probe x-ray
_diffrn_radiation_type MoK\a
_diffrn_radiation_wavelength 0.71073
_diffrn_reflns_av_R_equivalents 0.0428
_diffrn_reflns_av_unetI/netI 0.0744
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.875
_diffrn_reflns_limit_h_max 16
_diffrn_reflns_limit_h_min -17
_diffrn_reflns_limit_k_max 18
_diffrn_reflns_limit_k_min -18
_diffrn_reflns_limit_l_max 20
_diffrn_reflns_limit_l_min -19
_diffrn_reflns_number 16662
_diffrn_reflns_point_group_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.832
_diffrn_reflns_theta_full 25.242
_diffrn_reflns_theta_max 29.521
_diffrn_reflns_theta_min 3.476
_diffrn_source 'micro-focus sealed X-ray tube'
_diffrn_source_type 'SuperNova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu 1.400
_exptl_absorpt_correction_T_max 1.00000
_exptl_absorpt_correction_T_min 0.31306
_exptl_absorpt_correction_type multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.42.90a (Rigaku Oxford Diffraction, 2023)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_density_diffrn 1.336
_exptl_crystal_F_000 1136
_refine_diff_density_max 0.248
_refine_diff_density_min -0.314
_refine_diff_density_rms 0.048
_refine_ls_abs_structure_details
;
Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack -0.006(12)
_refine_ls_extinction_method none
_refine_ls_goodness_of_fit_ref 0.998
_refine_ls_hydrogen_treatment constr
_refine_ls_matrix_type full
_refine_ls_number_parameters 338
_refine_ls_number_reflns 6380
_refine_ls_number_restraints 0
_refine_ls_restrained_S_all 0.998
_refine_ls_R_factor_all 0.0942
_refine_ls_R_factor_gt 0.0474
_refine_ls_shift/su_max 0.001
_refine_ls_shift/su_mean 0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0360P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme calc
_refine_ls_wR_factor_gt 0.0827
_refine_ls_wR_factor_ref 0.0981
_reflns_Friedel_coverage 0.709
_reflns_Friedel_fraction_full 0.989
_reflns_Friedel_fraction_max 0.777
_reflns_number_gt 4030
_reflns_number_total 6380
_reflns_threshold_expression 'I > 2\s(I)'
_cod_data_source_file d4ob01498g2.cif
_cod_data_source_block zxq-1-3_auto
_cod_depositor_comments 'Adding full bibliography for 7160188.cif.'
_cod_database_code 7160188
_shelx_shelxl_version_number 2018/3
_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.
;
_reflns_odcompleteness_completeness 99.56
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta 26.32
_olex2_refinement_description
;
1. Twinned data refinement
Scales: 1.006(12)
-0.006(12)
2. Fixed Uiso
At 1.2 times of:
All C(H) groups, All C(H,H) groups
At 1.5 times of:
All C(H,H,H) groups, All O(H) groups
3.a Ternary CH refined with riding coordinates:
C00R(H00R)
3.b Secondary CH2 refined with riding coordinates:
C00I(H00B,H00C)
3.c Aromatic/amide H refined with riding coordinates:
C00A(H00A), C00D(H00D), C00E(H00E), C00F(H00F), C00G(H00G), C00J(H00J),
C00K(H00K), C00M(H00M), C00P(H00P), C00Q(H00Q), C00S(H00S), C00T(H00T),
C00U(H00U), C00V(H00V), C00W(H00W), C00X(H00X), C00Y(H00Y), C00Z(H00Z)
3.d Idealised Me refined as rotating group:
C010(H01A,H01B,H01C), C011(H01D,H01E,H01F)
3.e Idealised tetrahedral OH refined as rotating group:
O002(H002)
;
_shelx_res_file
;
TITL zxq-1-3_auto_a.res in P2(1)2(1)2(1)
zxq-1-3_auto.res
created by SHELXL-2018/3 at 21:39:32 on 28-Dec-2023
REM Old TITL ZXQ-1-3_auto in P2(1)2(1)2(1)
REM SHELXT solution in P2(1)2(1)2(1): R1 0.174, Rweak 0.056, Alpha 0.012
REM 1.148 for 23 systematic absences, Orientation as input
REM Flack x = 0.084 ( 0.006 ) from 1358 Parsons' quotients
REM Formula found by SHELXT: C31 N3 O2 Br
CELL 0.71073 12.5627 14.7048 14.8441 90 90 90
ZERR 12 0.0011 0.0007 0.0007 0 0 0
LATT -1
SYMM 0.5-X,-Y,0.5+Z
SYMM -X,0.5+Y,0.5-Z
SYMM 0.5+X,0.5-Y,-Z
SFAC C H N O Se
UNIT 128 112 8 8 4
L.S. 10
PLAN 20
BOND
list 4
fmap 2 53
ACTA
TWIN -1 0 0 0 -1 0 0 0 -1 2
REM
REM
REM
WGHT 0.036000
BASF -0.00614
FVAR 0.37337
SE01 5 0.308363 0.570601 0.384396 11.00000 0.09510 0.04281 =
0.05497 0.01079 0.01214 -0.00304
O002 4 0.547379 0.619499 0.316956 11.00000 0.06439 0.04266 =
0.06561 -0.00237 -0.01034 0.00746
AFIX 147
H002 2 0.560818 0.565554 0.325111 11.00000 -1.50000
AFIX 0
N003 3 0.342517 0.787451 0.203544 11.00000 0.05064 0.03259 =
0.03205 -0.00068 -0.00070 -0.00090
O004 4 0.292583 0.677424 0.102274 11.00000 0.12725 0.04389 =
0.04858 -0.00537 -0.00573 -0.02426
N005 3 0.405342 0.931206 0.155827 11.00000 0.06108 0.03671 =
0.03311 0.00107 -0.00123 -0.00185
C006 1 0.402726 0.900371 0.066448 11.00000 0.05403 0.03855 =
0.03352 0.00139 -0.00041 0.00424
C007 1 0.306807 0.729695 0.277633 11.00000 0.05132 0.03497 =
0.03657 0.00236 0.00043 -0.00205
C008 1 0.387840 0.907319 0.313549 11.00000 0.04058 0.03554 =
0.03499 -0.00041 -0.00089 -0.00496
C009 1 0.411507 0.975576 0.487197 11.00000 0.05873 0.05338 =
0.04027 -0.00688 0.00488 -0.00638
C00A 1 0.455371 0.865484 0.373664 11.00000 0.05340 0.04643 =
0.04909 -0.00751 -0.00331 0.00945
AFIX 43
H00A 2 0.492741 0.813678 0.356599 11.00000 -1.20000
AFIX 0
C00B 1 0.361121 0.654814 0.295324 11.00000 0.05592 0.04071 =
0.03752 0.00094 -0.00161 -0.00511
C00C 1 0.377963 0.875215 0.219126 11.00000 0.04134 0.03841 =
0.03610 -0.00101 -0.00265 0.00221
C00D 1 0.333180 0.984293 0.340241 11.00000 0.05525 0.03897 =
0.04159 -0.00203 -0.00609 0.00694
AFIX 43
H00D 2 0.289130 1.014437 0.299700 11.00000 -1.20000
AFIX 0
C00E 1 0.111914 0.799668 0.457815 11.00000 0.07240 0.05351 =
0.06344 -0.00014 0.01334 -0.00553
AFIX 43
H00E 2 0.110616 0.808076 0.519900 11.00000 -1.20000
AFIX 0
C00F 1 0.467573 0.900575 0.459438 11.00000 0.06547 0.05724 =
0.04308 -0.00033 -0.01995 0.00513
AFIX 43
H00F 2 0.514730 0.872787 0.499119 11.00000 -1.20000
AFIX 0
C00G 1 0.344067 1.016490 0.427416 11.00000 0.06475 0.05145 =
0.05163 -0.01469 0.00454 0.00649
AFIX 43
H00G 2 0.304784 1.066854 0.445602 11.00000 -1.20000
AFIX 0
C00H 1 0.300659 0.464711 0.308687 11.00000 0.05661 0.04006 =
0.08178 -0.00072 0.01852 -0.00271
C00I 1 0.465499 0.627767 0.251989 11.00000 0.06442 0.03723 =
0.04875 0.00016 0.00026 0.00379
AFIX 23
H00B 2 0.456656 0.570205 0.220963 11.00000 -1.20000
H00C 2 0.485551 0.673184 0.207740 11.00000 -1.20000
AFIX 0
C00J 1 0.022590 0.814936 0.408136 11.00000 0.06614 0.05545 =
0.08825 -0.00265 0.02586 -0.00281
AFIX 43
H00J 2 -0.040300 0.831780 0.436666 11.00000 -1.20000
AFIX 0
C00K 1 0.441250 0.957381 -0.000404 11.00000 0.07394 0.05907 =
0.04374 0.00523 0.00079 -0.01690
AFIX 43
H00K 2 0.466387 1.014949 0.014442 11.00000 -1.20000
AFIX 0
C00L 1 0.367800 0.812890 0.044582 11.00000 0.05324 0.04365 =
0.03450 -0.00634 -0.00170 0.00391
C00M 1 0.204680 0.771614 0.415838 11.00000 0.06198 0.04650 =
0.04973 0.00326 0.00402 0.00495
AFIX 43
H00M 2 0.265098 0.760115 0.450203 11.00000 -1.20000
AFIX 0
C00N 1 0.330930 0.752310 0.114700 11.00000 0.06121 0.03816 =
0.03934 -0.00364 0.00046 -0.00122
C00O 1 0.208549 0.760422 0.322781 11.00000 0.05088 0.03469 =
0.04328 0.00045 0.00070 -0.00283
C00P 1 0.442341 0.928930 -0.088604 11.00000 0.09856 0.06858 =
0.03938 0.00669 0.00422 -0.01079
AFIX 43
H00P 2 0.466834 0.967745 -0.133515 11.00000 -1.20000
AFIX 0
C00Q 1 0.407420 0.843528 -0.110432 11.00000 0.09359 0.07943 =
0.03133 -0.00458 0.00370 0.00645
AFIX 43
H00Q 2 0.409113 0.824691 -0.170222 11.00000 -1.20000
AFIX 0
C00R 1 0.423239 1.013634 0.582250 11.00000 0.10282 0.08899 =
0.04120 -0.01933 -0.00287 -0.00053
AFIX 13
H00R 2 0.379403 1.068760 0.582559 11.00000 -1.20000
AFIX 0
C00S 1 0.369775 0.784972 -0.045222 11.00000 0.08425 0.04927 =
0.04214 -0.00962 -0.00339 0.00229
AFIX 43
H00S 2 0.345872 0.727274 -0.061006 11.00000 -1.20000
AFIX 0
C00T 1 0.269137 0.470117 0.220284 11.00000 0.07399 0.06394 =
0.09356 -0.00984 0.01072 -0.01749
AFIX 43
H00T 2 0.252782 0.526323 0.195114 11.00000 -1.20000
AFIX 0
C00U 1 0.322784 0.381111 0.346900 11.00000 0.06065 0.04954 =
0.12189 0.01423 0.03136 0.00173
AFIX 43
H00U 2 0.343928 0.376820 0.406791 11.00000 -1.20000
AFIX 0
C00V 1 0.024894 0.805568 0.315880 11.00000 0.05312 0.06845 =
0.08221 0.00613 0.00523 0.00324
AFIX 43
H00V 2 -0.035824 0.817806 0.282151 11.00000 -1.20000
AFIX 0
C00W 1 0.117191 0.778032 0.273306 11.00000 0.05970 0.05934 =
0.05489 0.00023 0.00376 0.00250
AFIX 43
H00W 2 0.118084 0.771251 0.211021 11.00000 -1.20000
AFIX 0
C00X 1 0.312558 0.301742 0.292754 11.00000 0.08430 0.04479 =
0.17449 0.00366 0.05588 -0.00070
AFIX 43
H00X 2 0.326266 0.244662 0.317112 11.00000 -1.20000
AFIX 0
C00Y 1 0.282749 0.309966 0.205596 11.00000 0.10219 0.08118 =
0.17878 -0.03998 0.07957 -0.04354
AFIX 43
H00Y 2 0.276640 0.257915 0.170387 11.00000 -1.20000
AFIX 0
C00Z 1 0.261629 0.391754 0.168362 11.00000 0.08805 0.10050 =
0.10623 -0.03370 0.02961 -0.04103
AFIX 43
H00Z 2 0.242085 0.395646 0.108056 11.00000 -1.20000
AFIX 0
C010 1 0.375686 0.955539 0.649618 11.00000 0.22898 0.21242 =
0.05136 -0.01029 0.02913 -0.02374
AFIX 137
H01A 2 0.308915 0.932752 0.627717 11.00000 -1.50000
H01B 2 0.364026 0.989746 0.703810 11.00000 -1.50000
H01C 2 0.422515 0.905511 0.662097 11.00000 -1.50000
AFIX 0
C011 1 0.528373 1.044949 0.598881 11.00000 0.11277 0.40319 =
0.13689 -0.17666 0.00309 -0.06207
AFIX 137
H01D 2 0.573985 0.993934 0.610652 11.00000 -1.50000
H01E 2 0.528203 1.084742 0.650150 11.00000 -1.50000
H01F 2 0.553989 1.077335 0.547081 11.00000 -1.50000
AFIX 0
HKLF 4
REM zxq-1-3_auto_a.res in P2(1)2(1)2(1)
REM wR2 = 0.0981, GooF = S = 0.998, Restrained GooF = 0.998 for all data
REM R1 = 0.0474 for 4030 Fo > 4sig(Fo) and 0.0942 for all 6380 data
REM 338 parameters refined using 0 restraints
END
WGHT 0.0360 0.0000
REM Highest difference peak 0.248, deepest hole -0.314, 1-sigma level 0.048
Q1 1 0.4694 0.9353 0.6429 11.00000 0.05 0.25
Q2 1 0.5556 0.9367 0.6156 11.00000 0.05 0.23
Q3 1 0.3607 0.5204 0.2594 11.00000 0.05 0.21
Q4 1 0.4395 0.5034 0.3005 11.00000 0.05 0.20
Q5 1 0.1991 0.4417 0.0624 11.00000 0.05 0.20
Q6 1 0.2365 0.5756 0.3645 11.00000 0.05 0.19
Q7 1 0.4556 1.0813 0.5946 11.00000 0.05 0.19
Q8 1 -0.0743 0.7807 0.3829 11.00000 0.05 0.19
Q9 1 0.3161 0.6174 0.3208 11.00000 0.05 0.18
Q10 1 0.3246 0.2940 0.3796 11.00000 0.05 0.18
Q11 1 -0.1338 0.8845 0.4952 11.00000 0.05 0.18
Q12 1 0.1010 0.8798 0.3828 11.00000 0.05 0.17
Q13 1 0.3512 0.4121 0.4419 11.00000 0.05 0.17
Q14 1 0.2648 0.6370 0.3801 11.00000 0.05 0.17
Q15 1 0.3554 0.5005 0.3825 11.00000 0.05 0.17
Q16 1 0.4576 0.7831 0.3829 11.00000 0.05 0.16
Q17 1 0.3198 0.2458 0.3974 11.00000 0.05 0.16
Q18 1 0.5330 1.0097 0.6491 11.00000 0.05 0.16
Q19 1 0.3340 0.5147 0.3209 11.00000 0.05 0.16
Q20 1 0.4218 0.7970 0.2170 11.00000 0.05 0.15
;
_shelx_res_checksum 2789
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 2.259
_oxdiff_exptl_absorpt_empirical_full_min 0.597
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Se01 Se 0.30836(5) 0.57060(3) 0.38440(3) 0.0643(2) Uani 1 1 d . . . . .
O002 O 0.5474(3) 0.6195(2) 0.3170(2) 0.0576(9) Uani 1 1 d . . . . .
H002 H 0.560818 0.565554 0.325111 0.086 Uiso 1 1 calc GR . . . .
N003 N 0.3425(3) 0.7875(2) 0.2035(2) 0.0384(9) Uani 1 1 d . . . . .
O004 O 0.2926(4) 0.6774(2) 0.10227(19) 0.0732(12) Uani 1 1 d . . . . .
N005 N 0.4053(3) 0.9312(2) 0.1558(2) 0.0436(9) Uani 1 1 d . . . . .
C006 C 0.4027(4) 0.9004(3) 0.0664(3) 0.0420(12) Uani 1 1 d . . . . .
C007 C 0.3068(4) 0.7297(3) 0.2776(3) 0.0410(10) Uani 1 1 d . . . . .
C008 C 0.3878(4) 0.9073(3) 0.3135(3) 0.0370(11) Uani 1 1 d . . . . .
C009 C 0.4115(4) 0.9756(3) 0.4872(3) 0.0508(13) Uani 1 1 d . . . . .
C00A C 0.4554(4) 0.8655(3) 0.3737(3) 0.0496(12) Uani 1 1 d . . . . .
H00A H 0.492741 0.813678 0.356599 0.060 Uiso 1 1 calc R . . . .
C00B C 0.3611(4) 0.6548(3) 0.2953(3) 0.0447(12) Uani 1 1 d . . . . .
C00C C 0.3780(4) 0.8752(3) 0.2191(3) 0.0386(11) Uani 1 1 d . . . . .
C00D C 0.3332(4) 0.9843(3) 0.3402(3) 0.0453(12) Uani 1 1 d . . . . .
H00D H 0.289130 1.014437 0.299700 0.054 Uiso 1 1 calc R . . . .
C00E C 0.1119(5) 0.7997(3) 0.4578(4) 0.0631(16) Uani 1 1 d . . . . .
H00E H 0.110616 0.808076 0.519900 0.076 Uiso 1 1 calc R . . . .
C00F C 0.4676(5) 0.9006(3) 0.4594(3) 0.0553(14) Uani 1 1 d . . . . .
H00F H 0.514730 0.872787 0.499119 0.066 Uiso 1 1 calc R . . . .
C00G C 0.3441(4) 1.0165(3) 0.4274(3) 0.0559(15) Uani 1 1 d . . . . .
H00G H 0.304784 1.066854 0.445602 0.067 Uiso 1 1 calc R . . . .
C00H C 0.3007(5) 0.4647(3) 0.3087(4) 0.0595(14) Uani 1 1 d . . . . .
C00I C 0.4655(4) 0.6278(3) 0.2520(3) 0.0501(13) Uani 1 1 d . . . . .
H00B H 0.456656 0.570205 0.220963 0.060 Uiso 1 1 calc R . . . .
H00C H 0.485551 0.673184 0.207740 0.060 Uiso 1 1 calc R . . . .
C00J C 0.0226(5) 0.8149(4) 0.4081(4) 0.0699(17) Uani 1 1 d . . . . .
H00J H -0.040300 0.831780 0.436666 0.084 Uiso 1 1 calc R . . . .
C00K C 0.4412(5) 0.9574(3) -0.0004(3) 0.0589(14) Uani 1 1 d . . . . .
H00K H 0.466387 1.014949 0.014442 0.071 Uiso 1 1 calc R . . . .
C00L C 0.3678(4) 0.8129(3) 0.0446(3) 0.0438(12) Uani 1 1 d . . . . .
C00M C 0.2047(5) 0.7716(3) 0.4158(3) 0.0527(13) Uani 1 1 d . . . . .
H00M H 0.265098 0.760115 0.450203 0.063 Uiso 1 1 calc R . . . .
C00N C 0.3309(4) 0.7523(3) 0.1147(3) 0.0462(11) Uani 1 1 d . . . . .
C00O C 0.2085(4) 0.7604(3) 0.3228(3) 0.0429(12) Uani 1 1 d . . . . .
C00P C 0.4423(5) 0.9289(4) -0.0886(3) 0.0688(16) Uani 1 1 d . . . . .
H00P H 0.466834 0.967745 -0.133515 0.083 Uiso 1 1 calc R . . . .
C00Q C 0.4074(5) 0.8435(4) -0.1104(3) 0.0681(16) Uani 1 1 d . . . . .
H00Q H 0.409113 0.824691 -0.170222 0.082 Uiso 1 1 calc R . . . .
C00R C 0.4232(6) 1.0136(4) 0.5823(3) 0.0777(19) Uani 1 1 d . . . . .
H00R H 0.379403 1.068760 0.582559 0.093 Uiso 1 1 calc R . . . .
C00S C 0.3698(5) 0.7850(3) -0.0452(3) 0.0586(15) Uani 1 1 d . . . . .
H00S H 0.345872 0.727274 -0.061006 0.070 Uiso 1 1 calc R . . . .
C00T C 0.2691(5) 0.4701(4) 0.2203(4) 0.0772(18) Uani 1 1 d . . . . .
H00T H 0.252782 0.526323 0.195114 0.093 Uiso 1 1 calc R . . . .
C00U C 0.3228(5) 0.3811(3) 0.3469(4) 0.0774(18) Uani 1 1 d . . . . .
H00U H 0.343928 0.376820 0.406791 0.093 Uiso 1 1 calc R . . . .
C00V C 0.0249(5) 0.8056(4) 0.3159(4) 0.0679(16) Uani 1 1 d . . . . .
H00V H -0.035824 0.817806 0.282151 0.082 Uiso 1 1 calc R . . . .
C00W C 0.1172(5) 0.7780(3) 0.2733(4) 0.0580(14) Uani 1 1 d . . . . .
H00W H 0.118084 0.771251 0.211021 0.070 Uiso 1 1 calc R . . . .
C00X C 0.3126(7) 0.3017(4) 0.2928(6) 0.101(3) Uani 1 1 d . . . . .
H00X H 0.326266 0.244662 0.317112 0.121 Uiso 1 1 calc R . . . .
C00Y C 0.2827(7) 0.3100(6) 0.2056(7) 0.121(4) Uani 1 1 d . . . . .
H00Y H 0.276640 0.257915 0.170387 0.145 Uiso 1 1 calc R . . . .
C00Z C 0.2616(6) 0.3918(5) 0.1684(5) 0.098(2) Uani 1 1 d . . . . .
H00Z H 0.242085 0.395646 0.108056 0.118 Uiso 1 1 calc R . . . .
C010 C 0.3757(9) 0.9555(7) 0.6496(4) 0.164(4) Uani 1 1 d . . . . .
H01A H 0.308915 0.932752 0.627717 0.246 Uiso 1 1 calc GR . . . .
H01B H 0.364026 0.989746 0.703810 0.246 Uiso 1 1 calc GR . . . .
H01C H 0.422515 0.905511 0.662097 0.246 Uiso 1 1 calc GR . . . .
C011 C 0.5284(7) 1.0449(10) 0.5989(6) 0.218(7) Uani 1 1 d . . . . .
H01D H 0.573985 0.993934 0.610652 0.326 Uiso 1 1 calc GR . . . .
H01E H 0.528203 1.084742 0.650150 0.326 Uiso 1 1 calc GR . . . .
H01F H 0.553989 1.077335 0.547081 0.326 Uiso 1 1 calc GR . . . .
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
Se01 0.0951(5) 0.0428(2) 0.0550(3) 0.0108(2) 0.0121(3) -0.0030(3)
O002 0.064(3) 0.0427(17) 0.066(2) -0.0024(16) -0.010(2) 0.0075(18)
N003 0.051(3) 0.0326(17) 0.0321(18) -0.0007(14) -0.0007(17) -0.0009(17)
O004 0.127(4) 0.0439(17) 0.0486(18) -0.0054(15) -0.006(2) -0.024(2)
N005 0.061(3) 0.0367(18) 0.0331(18) 0.0011(17) -0.0012(18) -0.002(2)
C006 0.054(3) 0.039(2) 0.034(2) 0.0014(18) 0.000(2) 0.004(2)
C007 0.051(3) 0.035(2) 0.037(2) 0.0024(17) 0.000(3) -0.002(2)
C008 0.041(3) 0.036(2) 0.035(2) -0.0004(17) -0.001(2) -0.0050(19)
C009 0.059(4) 0.053(3) 0.040(3) -0.007(2) 0.005(3) -0.006(3)
C00A 0.053(3) 0.046(2) 0.049(3) -0.008(2) -0.003(3) 0.009(2)
C00B 0.056(3) 0.041(2) 0.038(2) 0.0009(19) -0.002(2) -0.005(2)
C00C 0.041(3) 0.038(2) 0.036(2) -0.0010(19) -0.003(2) 0.002(2)
C00D 0.055(4) 0.039(2) 0.042(2) -0.0020(19) -0.006(2) 0.007(2)
C00E 0.072(5) 0.054(3) 0.063(3) 0.000(3) 0.013(4) -0.006(3)
C00F 0.065(4) 0.057(3) 0.043(3) 0.000(2) -0.020(3) 0.005(3)
C00G 0.065(4) 0.051(3) 0.052(3) -0.015(2) 0.005(3) 0.006(3)
C00H 0.057(4) 0.040(2) 0.082(4) -0.001(2) 0.019(4) -0.003(3)
C00I 0.064(4) 0.037(2) 0.049(3) 0.000(2) 0.000(3) 0.004(2)
C00J 0.066(5) 0.055(3) 0.088(5) -0.003(3) 0.026(4) -0.003(3)
C00K 0.074(4) 0.059(3) 0.044(3) 0.005(2) 0.001(3) -0.017(3)
C00L 0.053(3) 0.044(2) 0.035(2) -0.006(2) -0.002(2) 0.004(2)
C00M 0.062(4) 0.046(2) 0.050(3) 0.003(2) 0.004(3) 0.005(3)
C00N 0.061(3) 0.038(2) 0.039(2) -0.004(2) 0.000(3) -0.001(2)
C00O 0.051(4) 0.035(2) 0.043(2) 0.0004(18) 0.001(3) -0.003(2)
C00P 0.099(5) 0.069(3) 0.039(3) 0.007(3) 0.004(3) -0.011(4)
C00Q 0.094(5) 0.079(4) 0.031(2) -0.005(3) 0.004(3) 0.006(3)
C00R 0.103(6) 0.089(4) 0.041(3) -0.019(3) -0.003(3) -0.001(4)
C00S 0.084(5) 0.049(3) 0.042(3) -0.010(2) -0.003(3) 0.002(3)
C00T 0.074(5) 0.064(3) 0.094(4) -0.010(3) 0.011(4) -0.017(3)
C00U 0.061(4) 0.050(3) 0.122(5) 0.014(3) 0.031(4) 0.002(3)
C00V 0.053(4) 0.068(4) 0.082(4) 0.006(3) 0.005(3) 0.003(3)
C00W 0.060(4) 0.059(3) 0.055(3) 0.000(2) 0.004(3) 0.002(3)
C00X 0.084(6) 0.045(3) 0.174(7) 0.004(4) 0.056(6) -0.001(4)
C00Y 0.102(7) 0.081(5) 0.179(8) -0.040(6) 0.080(7) -0.044(5)
C00Z 0.088(6) 0.101(5) 0.106(5) -0.034(5) 0.030(4) -0.041(4)
C010 0.229(12) 0.212(10) 0.051(4) -0.010(5) 0.029(6) -0.024(9)
C011 0.113(8) 0.403(18) 0.137(8) -0.177(10) 0.003(7) -0.062(10)
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'
Se Se -0.0929 2.2259 '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
C00H Se01 C00B 97.8(2) . . ?
C00C N003 C007 121.0(3) . . ?
C00C N003 C00N 121.7(3) . . ?
C00N N003 C007 117.1(3) . . ?
C00C N005 C006 118.3(4) . . ?
C00K C006 N005 118.3(4) . . ?
C00K C006 C00L 120.0(4) . . ?
C00L C006 N005 121.6(4) . . ?
N003 C007 C00O 114.9(3) . . ?
C00B C007 N003 118.4(4) . . ?
C00B C007 C00O 126.6(4) . . ?
C00A C008 C00C 121.4(4) . . ?
C00A C008 C00D 119.1(4) . . ?
C00D C008 C00C 119.3(4) . . ?
C00F C009 C00R 121.6(5) . . ?
C00G C009 C00F 118.5(4) . . ?
C00G C009 C00R 119.9(5) . . ?
C008 C00A C00F 119.9(4) . . ?
C007 C00B Se01 119.6(4) . . ?
C007 C00B C00I 125.6(4) . . ?
C00I C00B Se01 114.9(3) . . ?
N003 C00C C008 118.8(4) . . ?
N005 C00C N003 123.8(4) . . ?
N005 C00C C008 117.4(4) . . ?
C008 C00D C00G 119.9(4) . . ?
C00J C00E C00M 119.9(5) . . ?
C009 C00F C00A 121.3(4) . . ?
C009 C00G C00D 121.2(5) . . ?
C00T C00H Se01 121.8(4) . . ?
C00T C00H C00U 120.1(5) . . ?
C00U C00H Se01 118.1(4) . . ?
O002 C00I C00B 111.3(4) . . ?
C00E C00J C00V 120.3(6) . . ?
C00P C00K C006 120.1(5) . . ?
C006 C00L C00N 120.0(3) . . ?
C00S C00L C006 119.2(4) . . ?
C00S C00L C00N 120.8(4) . . ?
C00E C00M C00O 120.7(6) . . ?
N003 C00N C00L 114.2(3) . . ?
O004 C00N N003 120.6(4) . . ?
O004 C00N C00L 125.1(4) . . ?
C00M C00O C007 121.1(5) . . ?
C00W C00O C007 120.6(4) . . ?
C00W C00O C00M 118.3(5) . . ?
C00Q C00P C00K 120.1(5) . . ?
C00P C00Q C00S 121.1(4) . . ?
C010 C00R C009 112.6(5) . . ?
C011 C00R C009 111.7(6) . . ?
C011 C00R C010 117.1(8) . . ?
C00Q C00S C00L 119.5(4) . . ?
C00H C00T C00Z 120.1(6) . . ?
C00H C00U C00X 118.7(6) . . ?
C00J C00V C00W 120.1(6) . . ?
C00V C00W C00O 120.5(5) . . ?
C00Y C00X C00U 119.5(7) . . ?
C00Z C00Y C00X 121.7(7) . . ?
C00Y C00Z C00T 119.9(7) . . ?
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
Se01 C00B 1.929(4) . ?
Se01 C00H 1.923(5) . ?
O002 C00I 1.415(6) . ?
N003 C007 1.460(5) . ?
N003 C00C 1.385(5) . ?
N003 C00N 1.424(5) . ?
O004 C00N 1.216(5) . ?
N005 C006 1.402(5) . ?
N005 C00C 1.296(5) . ?
C006 C00K 1.386(6) . ?
C006 C00L 1.397(6) . ?
C007 C00B 1.322(6) . ?
C007 C00O 1.475(7) . ?
C008 C00A 1.376(6) . ?
C008 C00C 1.484(6) . ?
C008 C00D 1.382(6) . ?
C009 C00F 1.372(6) . ?
C009 C00G 1.366(7) . ?
C009 C00R 1.525(6) . ?
C00A C00F 1.382(6) . ?
C00B C00I 1.514(7) . ?
C00D C00G 1.385(6) . ?
C00E C00J 1.361(8) . ?
C00E C00M 1.384(7) . ?
C00H C00T 1.373(7) . ?
C00H C00U 1.382(7) . ?
C00J C00V 1.377(8) . ?
C00K C00P 1.375(6) . ?
C00L C00N 1.446(6) . ?
C00L C00S 1.395(6) . ?
C00M C00O 1.392(6) . ?
C00O C00W 1.387(7) . ?
C00P C00Q 1.369(7) . ?
C00Q C00S 1.379(7) . ?
C00R C010 1.445(10) . ?
C00R C011 1.420(10) . ?
C00T C00Z 1.390(8) . ?
C00U C00X 1.423(8) . ?
C00V C00W 1.381(7) . ?
C00X C00Y 1.352(10) . ?
C00Y C00Z 1.350(10) . ?
loop_
_twin_individual_id
_twin_individual_mass_fraction_refined
1 1.006(12)
2 -0.006(12)