#------------------------------------------------------------------------------
#$Date: 2019-11-11 20:31:44 +0200 (Mon, 11 Nov 2019) $
#$Revision: 227282 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/03/58/4035870.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_4035870
loop_
_publ_author_name
'Kotha, Sambasivarao'
'Cheekatla, Subba Rao'
_publ_section_title
;
Molecular Acrobatics in Polycyclic Frames: Synthesis of Functionalized
D3-Trishomocubanes via the Rearrangement Approach.
;
_journal_issue 12
_journal_name_full 'The Journal of organic chemistry'
_journal_page_first 6315
_journal_page_last 6324
_journal_paper_doi 10.1021/acs.joc.8b00449
_journal_volume 83
_journal_year 2018
_chemical_formula_moiety 'C16 H18 O2'
_chemical_formula_sum 'C16 H18 O2'
_chemical_formula_weight 242.30
_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'
_atom_sites_solution_hydrogens geom
_atom_sites_solution_primary dual
_audit_creation_date 2017-10-12
_audit_creation_method
;
Olex2 1.2-ac3
(compiled 2017.02.24 svn.r3390 for Rigaku Oxford Diffraction, GUI svn.r5318)
;
_cell_angle_alpha 90
_cell_angle_beta 97.019(6)
_cell_angle_gamma 90
_cell_formula_units_Z 4
_cell_length_a 7.3329(5)
_cell_length_b 11.9990(8)
_cell_length_c 13.2043(9)
_cell_measurement_reflns_used 2457
_cell_measurement_temperature 150
_cell_measurement_theta_max 31.0310
_cell_measurement_theta_min 2.2930
_cell_volume 1153.11(14)
_computing_cell_refinement 'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_computing_data_collection 'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_computing_data_reduction 'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_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 'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature 150
_diffrn_detector 'CCD plate'
_diffrn_detector_area_resol_mean 28.5714
_diffrn_detector_type 'Rigaku Saturn724+'
_diffrn_measured_fraction_theta_full 0.983
_diffrn_measured_fraction_theta_max 0.983
_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 -88.00 39.00 0.50 8.00 -- -20.00 0.00 -36.00 254
2 \w -105.00 -57.50 0.50 8.00 -- -20.00 0.00 108.00 95
;
_diffrn_measurement_device 'abstract diffractometer'
_diffrn_measurement_device_type
'dtrek-CrysAlisPro-abstract goniometer imported rigaku-d*trek images'
_diffrn_measurement_method '\w scans'
_diffrn_measurement_specimen_support 'Mitegen 50um'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11 -0.0126239000
_diffrn_orient_matrix_UB_12 -0.0434808000
_diffrn_orient_matrix_UB_13 -0.0365424000
_diffrn_orient_matrix_UB_21 -0.0841848000
_diffrn_orient_matrix_UB_22 -0.0145516000
_diffrn_orient_matrix_UB_23 0.0179564000
_diffrn_orient_matrix_UB_31 -0.0474841000
_diffrn_orient_matrix_UB_32 0.0373015000
_diffrn_orient_matrix_UB_33 -0.0356495000
_diffrn_radiation_collimation 0.3
_diffrn_radiation_monochromator graphite
_diffrn_radiation_probe x-ray
_diffrn_radiation_type MoK\a
_diffrn_radiation_wavelength 0.71073
_diffrn_reflns_av_R_equivalents 0.0480
_diffrn_reflns_av_unetI/netI 0.0635
_diffrn_reflns_Laue_measured_fraction_full 0.983
_diffrn_reflns_Laue_measured_fraction_max 0.983
_diffrn_reflns_limit_h_max 8
_diffrn_reflns_limit_h_min -5
_diffrn_reflns_limit_k_max 14
_diffrn_reflns_limit_k_min -13
_diffrn_reflns_limit_l_max 14
_diffrn_reflns_limit_l_min -15
_diffrn_reflns_number 3694
_diffrn_reflns_point_group_measured_fraction_full 0.983
_diffrn_reflns_point_group_measured_fraction_max 0.983
_diffrn_reflns_theta_full 24.994
_diffrn_reflns_theta_max 24.994
_diffrn_reflns_theta_min 2.301
_diffrn_source 'fine-focus sealed X-ray tube'
_diffrn_source_current 24.0
_diffrn_source_power 1.2
_diffrn_source_target Mo
_diffrn_source_type 'Enhance (Mo) X-ray Source'
_diffrn_source_voltage 50.0
_exptl_absorpt_coefficient_mu 0.090
_exptl_absorpt_correction_T_max 1.00000
_exptl_absorpt_correction_T_min 0.83890
_exptl_absorpt_correction_type multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.43 (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour colourless
_exptl_crystal_colour_primary colourless
_exptl_crystal_density_diffrn 1.396
_exptl_crystal_description block
_exptl_crystal_F_000 520
_exptl_crystal_size_max 0.173
_exptl_crystal_size_mid 0.153
_exptl_crystal_size_min 0.13
_refine_diff_density_max 0.267
_refine_diff_density_min -0.359
_refine_diff_density_rms 0.088
_refine_ls_extinction_method none
_refine_ls_goodness_of_fit_ref 1.057
_refine_ls_hydrogen_treatment constr
_refine_ls_matrix_type full
_refine_ls_number_parameters 164
_refine_ls_number_reflns 2000
_refine_ls_number_restraints 0
_refine_ls_restrained_S_all 1.057
_refine_ls_R_factor_all 0.0643
_refine_ls_R_factor_gt 0.0459
_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^)+(0.0451P)^2^+0.3748P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme calc
_refine_ls_wR_factor_gt 0.1016
_refine_ls_wR_factor_ref 0.1104
_reflns_Friedel_coverage 0.000
_reflns_number_gt 1652
_reflns_number_total 2000
_reflns_threshold_expression 'I > 2\s(I)'
_iucr_refine_instructions_details
;
srk-sr-452_mo.res created by SHELXL-2014/7
TITL srk-sr-452_mo_a.res in P2(1)/n
REM Old TITL srk-sr-452_mo_a.res in P2(1)/n
REM SHELXT solution in P2(1)/n
REM R1 0.188, Rweak 0.008, Alpha 0.032, Orientation as input
REM Formula found by SHELXT: C16 O2
CELL 0.71073 7.332855 11.999029 13.204254 90 97.0188 90
ZERR 4 0.000475 0.000812 0.000923 0 0.0063 0
LATT 1
SYMM 0.5-X,0.5+Y,0.5-Z
SFAC C H O
UNIT 64 72 8
L.S. 100
PLAN 10
TEMP -123.15
BOND $H
list 4
MORE -1
CONF
fmap 2
acta 52
OMIT -3 50
OMIT -1 1 1
OMIT -1 0 1
OMIT 0 0 2
OMIT 1 1 0
OMIT 0 2 0
OMIT -1 1 2
REM
REM
REM
WGHT 0.045100 0.374800
FVAR 5.94391
O1 3 0.447253 0.656094 0.611852 11.00000 0.03591 0.02193 =
0.02832 0.00310 0.00551 -0.00340
O2 3 0.479654 0.533952 0.856527 11.00000 0.01971 0.02681 =
0.02097 -0.00387 0.00281 -0.00017
C2 1 0.136964 0.341650 0.709637 11.00000 0.02282 0.02206 =
0.02434 -0.00037 0.00509 -0.00164
AFIX 13
H2 2 0.054363 0.303706 0.753769 11.00000 -1.20000
AFIX 0
C1 1 0.069930 0.342786 0.595960 11.00000 0.02413 0.02495 =
0.02603 -0.00337 0.00249 -0.00148
AFIX 23
H1A 2 -0.052881 0.377290 0.580129 11.00000 -1.20000
H1B 2 0.071358 0.267981 0.564436 11.00000 -1.20000
AFIX 0
C12 1 0.625375 0.304545 0.846356 11.00000 0.02904 0.02603 =
0.02382 0.00534 0.00103 0.00514
AFIX 23
H12A 2 0.685484 0.288684 0.784739 11.00000 -1.20000
H12B 2 0.634362 0.236872 0.889569 11.00000 -1.20000
AFIX 0
C10 1 0.188460 0.466192 0.738749 11.00000 0.01919 0.02080 =
0.02069 -0.00096 0.00470 0.00152
AFIX 13
H10 2 0.106277 0.503756 0.783356 11.00000 -1.20000
AFIX 0
C15 1 0.690804 0.499207 0.734884 11.00000 0.02115 0.02502 =
0.02360 -0.00005 0.00369 0.00006
AFIX 23
H15A 2 0.731658 0.569617 0.705711 11.00000 -1.20000
H15B 2 0.777045 0.438825 0.721999 11.00000 -1.20000
AFIX 0
C11 1 0.423698 0.333241 0.815086 11.00000 0.02544 0.02235 =
0.01990 0.00337 0.00611 0.00279
AFIX 13
H11 2 0.348734 0.313148 0.870784 11.00000 -1.20000
AFIX 0
C5 1 0.224633 0.417582 0.568636 11.00000 0.02559 0.02360 =
0.01795 -0.00164 0.00085 -0.00009
AFIX 13
H5 2 0.227704 0.430634 0.494065 11.00000 -1.20000
AFIX 0
C16 1 0.781189 0.609025 0.902316 11.00000 0.02637 0.03802 =
0.03022 -0.00705 0.00198 -0.00364
AFIX 137
H16A 2 0.735949 0.678523 0.869277 11.00000 -1.50000
H16B 2 0.912239 0.600484 0.896019 11.00000 -1.50000
H16C 2 0.763517 0.611206 0.974666 11.00000 -1.50000
AFIX 0
C7 1 0.389133 0.568515 0.640446 11.00000 0.02814 0.02108 =
0.01503 -0.00258 0.00545 0.00077
C4 1 0.407259 0.367840 0.628777 11.00000 0.02243 0.02038 =
0.02001 -0.00216 0.00529 0.00105
AFIX 13
H4 2 0.490323 0.328911 0.585547 11.00000 -1.20000
AFIX 0
C3 1 0.330525 0.292435 0.712811 11.00000 0.02620 0.01796 =
0.02435 0.00060 0.00615 0.00125
AFIX 13
H3 2 0.336159 0.210204 0.701277 11.00000 -1.20000
AFIX 0
C8 1 0.494750 0.470428 0.690917 11.00000 0.01817 0.02098 =
0.01997 0.00037 0.00424 0.00102
C6 1 0.198355 0.522899 0.633043 11.00000 0.02206 0.02090 =
0.02297 0.00201 0.00021 0.00362
AFIX 13
H6 2 0.095676 0.574309 0.607365 11.00000 -1.20000
AFIX 0
C13 1 0.723777 0.401409 0.905413 11.00000 0.02483 0.03722 =
0.02196 0.00276 0.00158 0.00578
AFIX 23
H13A 2 0.687109 0.404108 0.975084 11.00000 -1.20000
H13B 2 0.858241 0.389385 0.911509 11.00000 -1.20000
AFIX 0
C14 1 0.676170 0.511713 0.851428 11.00000 0.01789 0.03041 =
0.02238 -0.00266 0.00315 0.00094
C9 1 0.394706 0.455571 0.785443 11.00000 0.01994 0.02124 =
0.01750 -0.00187 0.00365 0.00132
HKLF 4
REM srk-sr-452_mo_a.res in P2(1)/n
REM R1 = 0.0459 for 1652 Fo > 4sig(Fo) and 0.0643 for all 2000 data
REM 164 parameters refined using 0 restraints
END
WGHT 0.0451 0.3748
REM Highest difference peak 0.267, deepest hole -0.359, 1-sigma level 0.088
Q1 1 0.5804 0.4839 0.7048 11.00000 0.05 0.27
Q2 1 0.5903 0.6618 0.7187 11.00000 0.05 0.26
Q3 1 0.5023 0.6179 0.8114 11.00000 0.05 0.26
Q4 1 0.4397 0.5238 0.6903 11.00000 0.05 0.26
Q5 1 0.4998 0.6251 0.7639 11.00000 0.05 0.25
Q6 1 0.1874 0.1368 0.7430 11.00000 0.05 0.24
Q7 1 0.4053 0.6027 0.8192 11.00000 0.05 0.23
Q8 1 0.6125 0.6095 0.7308 11.00000 0.05 0.23
Q9 1 0.3993 0.5790 0.7618 11.00000 0.05 0.23
Q10 1 0.1245 0.1589 0.7183 11.00000 0.05 0.23
REM The information below was added by Olex2.
REM
REM R1 = 0.0459 for 1652 Fo > 4sig(Fo) and 0.0643 for all 5322 data
REM n/a parameters refined using n/a restraints
REM Highest difference peak 0.27, deepest hole -0.36
REM Mean Shift 0, Max Shift 0.000.
REM +++ Tabular Listing of Refinement Information +++
REM R1_all = 0.0643
REM R1_gt = 0.0459
REM wR_ref = 0.1104
REM GOOF = 1.057
REM Shift_max = 0.000
REM Shift_mean = 0
REM Reflections_all = 5322
REM Reflections_gt = 1652
REM Parameters = n/a
REM Hole = -0.36
REM Peak = 0.27
REM Flack = n/a
;
_cod_data_source_file jo8b00449_si_003.cif
_cod_data_source_block srk-sr-452_mo
_cod_original_cell_volume 1153.10(14)
_cod_database_code 4035870
_shelx_shelxl_version_number 2014/7
_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 85.03
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta 30.99
_olex2_refinement_description
;
1. 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
2.a Ternary CH refined with riding coordinates:
C2(H2), C10(H10), C11(H11), C5(H5), C4(H4), C3(H3), C6(H6)
2.b Secondary CH2 refined with riding coordinates:
C1(H1A,H1B), C12(H12A,H12B), C15(H15A,H15B), C13(H13A,H13B)
2.c Idealised Me refined as rotating group:
C16(H16A,H16B,H16C)
;
_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
- Detector area scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.417
_oxdiff_exptl_absorpt_empirical_full_min 0.815
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_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
O1 O 0.44725(18) 0.65609(10) 0.61185(9) 0.0286(4) Uani 1 1 d .
O2 O 0.47965(16) 0.53395(10) 0.85653(9) 0.0225(3) Uani 1 1 d .
C2 C 0.1370(2) 0.34165(15) 0.70964(13) 0.0229(4) Uani 1 1 d .
H2 H 0.0544 0.3037 0.7538 0.027 Uiso 1 1 calc R
C1 C 0.0699(2) 0.34279(15) 0.59596(13) 0.0251(4) Uani 1 1 d .
H1A H -0.0529 0.3773 0.5801 0.030 Uiso 1 1 calc R
H1B H 0.0714 0.2680 0.5644 0.030 Uiso 1 1 calc R
C12 C 0.6254(3) 0.30455(15) 0.84636(14) 0.0265(5) Uani 1 1 d .
H12A H 0.6855 0.2887 0.7847 0.032 Uiso 1 1 calc R
H12B H 0.6344 0.2369 0.8896 0.032 Uiso 1 1 calc R
C10 C 0.1885(2) 0.46619(14) 0.73875(13) 0.0200(4) Uani 1 1 d .
H10 H 0.1063 0.5038 0.7834 0.024 Uiso 1 1 calc R
C15 C 0.6908(2) 0.49921(16) 0.73488(13) 0.0232(4) Uani 1 1 d .
H15A H 0.7317 0.5696 0.7057 0.028 Uiso 1 1 calc R
H15B H 0.7770 0.4388 0.7220 0.028 Uiso 1 1 calc R
C11 C 0.4237(2) 0.33324(14) 0.81509(13) 0.0223(4) Uani 1 1 d .
H11 H 0.3487 0.3131 0.8708 0.027 Uiso 1 1 calc R
C5 C 0.2246(2) 0.41758(14) 0.56864(13) 0.0225(4) Uani 1 1 d .
H5 H 0.2277 0.4306 0.4941 0.027 Uiso 1 1 calc R
C16 C 0.7812(3) 0.60903(17) 0.90232(15) 0.0317(5) Uani 1 1 d .
H16A H 0.7359 0.6785 0.8693 0.047 Uiso 1 1 calc GR
H16B H 0.9122 0.6005 0.8960 0.047 Uiso 1 1 calc GR
H16C H 0.7635 0.6112 0.9747 0.047 Uiso 1 1 calc GR
C7 C 0.3891(2) 0.56852(15) 0.64045(12) 0.0212(4) Uani 1 1 d .
C4 C 0.4073(2) 0.36784(14) 0.62878(13) 0.0207(4) Uani 1 1 d .
H4 H 0.4903 0.3289 0.5855 0.025 Uiso 1 1 calc R
C3 C 0.3305(2) 0.29244(15) 0.71281(13) 0.0226(4) Uani 1 1 d .
H3 H 0.3362 0.2102 0.7013 0.027 Uiso 1 1 calc R
C8 C 0.4948(2) 0.47043(14) 0.69092(13) 0.0195(4) Uani 1 1 d .
C6 C 0.1984(2) 0.52290(14) 0.63304(13) 0.0222(4) Uani 1 1 d .
H6 H 0.0957 0.5743 0.6074 0.027 Uiso 1 1 calc R
C13 C 0.7238(3) 0.40141(16) 0.90541(14) 0.0281(5) Uani 1 1 d .
H13A H 0.6871 0.4041 0.9751 0.034 Uiso 1 1 calc R
H13B H 0.8582 0.3894 0.9115 0.034 Uiso 1 1 calc R
C14 C 0.6762(2) 0.51171(15) 0.85143(13) 0.0235(4) Uani 1 1 d .
C9 C 0.3947(2) 0.45557(15) 0.78544(12) 0.0194(4) Uani 1 1 d .
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
O1 0.0359(8) 0.0219(7) 0.0283(7) 0.0031(6) 0.0055(6) -0.0034(6)
O2 0.0197(7) 0.0268(7) 0.0210(6) -0.0039(5) 0.0028(5) -0.0002(5)
C2 0.0228(10) 0.0221(9) 0.0243(9) -0.0004(8) 0.0051(8) -0.0016(8)
C1 0.0241(10) 0.0249(10) 0.0260(10) -0.0034(8) 0.0025(8) -0.0015(8)
C12 0.0290(11) 0.0260(10) 0.0238(10) 0.0053(8) 0.0010(8) 0.0051(8)
C10 0.0192(9) 0.0208(9) 0.0207(9) -0.0010(7) 0.0047(7) 0.0015(7)
C15 0.0211(10) 0.0250(9) 0.0236(10) 0.0000(8) 0.0037(8) 0.0001(8)
C11 0.0254(10) 0.0224(10) 0.0199(9) 0.0034(8) 0.0061(8) 0.0028(8)
C5 0.0256(10) 0.0236(9) 0.0179(9) -0.0016(8) 0.0009(7) -0.0001(8)
C16 0.0264(11) 0.0380(12) 0.0302(11) -0.0070(9) 0.0020(8) -0.0036(9)
C7 0.0281(10) 0.0211(9) 0.0150(9) -0.0026(7) 0.0054(7) 0.0008(8)
C4 0.0224(9) 0.0204(9) 0.0200(9) -0.0022(7) 0.0053(7) 0.0010(7)
C3 0.0262(10) 0.0180(9) 0.0244(9) 0.0006(8) 0.0062(8) 0.0013(8)
C8 0.0182(9) 0.0210(9) 0.0200(9) 0.0004(8) 0.0042(7) 0.0010(7)
C6 0.0221(9) 0.0209(9) 0.0230(9) 0.0020(8) 0.0002(8) 0.0036(8)
C13 0.0248(10) 0.0372(11) 0.0220(9) 0.0028(9) 0.0016(8) 0.0058(9)
C14 0.0179(9) 0.0304(10) 0.0224(10) -0.0027(8) 0.0031(8) 0.0009(8)
C9 0.0199(9) 0.0212(9) 0.0175(9) -0.0019(7) 0.0037(7) 0.0013(7)
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'
O O 0.0106 0.0060 '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
C9 O2 C14 101.68(12)
C1 C2 H2 115.7
C1 C2 C10 105.71(14)
C1 C2 C3 102.52(14)
C10 C2 H2 115.7
C3 C2 H2 115.7
C3 C2 C10 99.50(13)
C2 C1 H1A 112.8
C2 C1 H1B 112.8
C2 C1 C5 94.52(14)
H1A C1 H1B 110.3
C5 C1 H1A 112.8
C5 C1 H1B 112.8
H12A C12 H12B 108.1
C11 C12 H12A 109.6
C11 C12 H12B 109.6
C11 C12 C13 110.34(15)
C13 C12 H12A 109.6
C13 C12 H12B 109.6
C2 C10 H10 115.3
C6 C10 C2 103.34(13)
C6 C10 H10 115.3
C6 C10 C9 103.83(13)
C9 C10 C2 102.10(13)
C9 C10 H10 115.3
H15A C15 H15B 109.1
C8 C15 H15A 111.2
C8 C15 H15B 111.2
C8 C15 C14 102.82(13)
C14 C15 H15A 111.2
C14 C15 H15B 111.2
C12 C11 H11 110.4
C12 C11 C9 112.72(15)
C3 C11 C12 118.95(15)
C3 C11 H11 110.4
C3 C11 C9 92.78(13)
C9 C11 H11 110.4
C1 C5 H5 115.6
C1 C5 C4 105.49(13)
C1 C5 C6 101.79(14)
C4 C5 H5 115.6
C6 C5 H5 115.6
C6 C5 C4 100.72(13)
H16A C16 H16B 109.5
H16A C16 H16C 109.5
H16B C16 H16C 109.5
C14 C16 H16A 109.5
C14 C16 H16B 109.5
C14 C16 H16C 109.5
O1 C7 C8 129.01(17)
O1 C7 C6 131.26(17)
C6 C7 C8 99.68(14)
C5 C4 H4 115.2
C3 C4 C5 102.39(13)
C3 C4 H4 115.2
C8 C4 C5 103.43(13)
C8 C4 H4 115.2
C8 C4 C3 103.79(13)
C2 C3 C4 99.64(14)
C2 C3 H3 115.5
C11 C3 C2 102.39(14)
C11 C3 C4 106.18(14)
C11 C3 H3 115.5
C4 C3 H3 115.5
C15 C8 C4 133.04(15)
C15 C8 C9 103.85(14)
C7 C8 C15 113.51(14)
C7 C8 C4 102.96(13)
C7 C8 C9 100.27(13)
C9 C8 C4 97.38(13)
C10 C6 H6 117.1
C5 C6 C10 99.07(13)
C5 C6 H6 117.1
C7 C6 C10 104.26(13)
C7 C6 C5 99.01(14)
C7 C6 H6 117.1
C12 C13 H13A 109.5
C12 C13 H13B 109.5
H13A C13 H13B 108.1
C14 C13 C12 110.77(14)
C14 C13 H13A 109.5
C14 C13 H13B 109.5
O2 C14 C15 104.32(13)
O2 C14 C16 106.72(14)
O2 C14 C13 107.76(14)
C16 C14 C15 114.81(15)
C16 C14 C13 112.84(15)
C13 C14 C15 109.75(15)
O2 C9 C10 122.09(14)
O2 C9 C11 115.57(14)
O2 C9 C8 104.27(13)
C11 C9 C10 106.05(14)
C11 C9 C8 104.77(13)
C8 C9 C10 101.83(13)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O1 C7 1.212(2)
O2 C14 1.475(2)
O2 C9 1.418(2)
C2 H2 1.0000
C2 C1 1.521(2)
C2 C10 1.577(2)
C2 C3 1.533(2)
C1 H1A 0.9900
C1 H1B 0.9900
C1 C5 1.524(2)
C12 H12A 0.9900
C12 H12B 0.9900
C12 C11 1.525(2)
C12 C13 1.530(3)
C10 H10 1.0000
C10 C6 1.562(2)
C10 C9 1.567(2)
C15 H15A 0.9900
C15 H15B 0.9900
C15 C8 1.523(2)
C15 C14 1.563(2)
C11 H11 1.0000
C11 C3 1.518(2)
C11 C9 1.527(2)
C5 H5 1.0000
C5 C4 1.588(2)
C5 C6 1.548(2)
C16 H16A 0.9800
C16 H16B 0.9800
C16 H16C 0.9800
C16 C14 1.510(3)
C7 C8 1.518(2)
C7 C6 1.494(2)
C4 H4 1.0000
C4 C3 1.587(2)
C4 C8 1.572(2)
C3 H3 1.0000
C8 C9 1.533(2)
C6 H6 1.0000
C13 H13A 0.9900
C13 H13B 0.9900
C13 C14 1.523(3)
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
O1 C7 C8 C15 17.2(3)
O1 C7 C8 C4 -132.55(18)
O1 C7 C8 C9 127.34(19)
O1 C7 C6 C10 -139.04(19)
O1 C7 C6 C5 119.1(2)
C2 C1 C5 C4 45.86(15)
C2 C1 C5 C6 -58.92(15)
C2 C10 C6 C5 -20.27(15)
C2 C10 C6 C7 -122.05(14)
C2 C10 C9 O2 -155.05(15)
C2 C10 C9 C11 -19.77(16)
C2 C10 C9 C8 89.58(15)
C1 C2 C10 C6 -15.38(17)
C1 C2 C10 C9 -122.96(14)
C1 C2 C3 C11 158.03(14)
C1 C2 C3 C4 48.97(16)
C1 C5 C4 C3 -17.79(16)
C1 C5 C4 C8 -125.45(14)
C1 C5 C6 C10 50.31(15)
C1 C5 C6 C7 156.45(14)
C12 C11 C3 C2 -178.01(15)
C12 C11 C3 C4 -73.99(19)
C12 C11 C9 O2 -50.51(19)
C12 C11 C9 C10 170.86(13)
C12 C11 C9 C8 63.62(18)
C12 C13 C14 O2 66.86(18)
C12 C13 C14 C15 -46.2(2)
C12 C13 C14 C16 -175.58(16)
C10 C2 C1 C5 44.50(16)
C10 C2 C3 C11 49.47(16)
C10 C2 C3 C4 -59.60(15)
C15 C8 C9 O2 34.05(17)
C15 C8 C9 C10 161.89(13)
C15 C8 C9 C11 -87.80(15)
C11 C12 C13 C14 -46.3(2)
C5 C4 C3 C2 -17.97(16)
C5 C4 C3 C11 -123.99(14)
C5 C4 C8 C15 -155.39(17)
C5 C4 C8 C7 -14.59(16)
C5 C4 C8 C9 87.79(14)
C7 C8 C9 O2 -83.48(15)
C7 C8 C9 C10 44.36(15)
C7 C8 C9 C11 154.68(13)
C4 C5 C6 C10 -58.18(15)
C4 C5 C6 C7 47.96(15)
C4 C8 C9 O2 171.85(12)
C4 C8 C9 C10 -60.32(15)
C4 C8 C9 C11 50.00(16)
C3 C2 C1 C5 -59.28(15)
C3 C2 C10 C6 90.61(15)
C3 C2 C10 C9 -16.97(16)
C3 C11 C9 O2 -173.58(14)
C3 C11 C9 C10 47.79(15)
C3 C11 C9 C8 -59.46(15)
C3 C4 C8 C15 98.0(2)
C3 C4 C8 C7 -121.19(14)
C3 C4 C8 C9 -18.81(15)
C8 C15 C14 O2 -21.60(17)
C8 C15 C14 C16 -138.03(15)
C8 C15 C14 C13 93.63(16)
C8 C7 C6 C10 43.36(16)
C8 C7 C6 C5 -58.47(14)
C8 C4 C3 C2 89.41(15)
C8 C4 C3 C11 -16.60(17)
C6 C10 C9 O2 97.75(17)
C6 C10 C9 C11 -126.97(14)
C6 C10 C9 C8 -17.63(16)
C6 C5 C4 C3 87.78(15)
C6 C5 C4 C8 -19.88(16)
C6 C7 C8 C15 -165.11(14)
C6 C7 C8 C4 45.13(15)
C6 C7 C8 C9 -54.99(15)
C13 C12 C11 C3 143.89(16)
C13 C12 C11 C9 36.9(2)
C14 O2 C9 C10 -162.31(15)
C14 O2 C9 C11 66.26(17)
C14 O2 C9 C8 -48.15(15)
C14 C15 C8 C7 101.40(16)
C14 C15 C8 C4 -120.80(19)
C14 C15 C8 C9 -6.52(17)
C9 O2 C14 C15 43.52(16)
C9 O2 C14 C16 165.45(14)
C9 O2 C14 C13 -73.09(15)
C9 C10 C6 C5 86.00(15)
C9 C10 C6 C7 -15.78(17)
C9 C11 C3 C2 -60.05(15)
C9 C11 C3 C4 43.97(15)
loop_
_refln_index_h
_refln_index_k
_refln_index_l
_refln_F_squared_meas
_refln_F_squared_sigma
_refln_scale_group_code
0 0 -2 4.6098 6.11808 1
0 0 -3 -15.3788 16.6669 1
0 0 3 70.7063 29.0249 1
0 0 -5 14.0027 16.3509 1
0 0 -6 20476.9 591.149 1
0 0 -7 7.68631 21.986 2
0 0 -7 32.1181 29.9223 1
0 0 -8 34849.2 865.122 2
0 0 -9 14.6785 49.3621 2
0 0 -10 2155.26 242.549 2
0 0 -11 -53.8384 69.4452 2
0 0 -12 4668.1 400.552 2
0 0 -13 32.5377 62.5409 2
0 0 -14 9939.29 630.113 2
0 0 -15 131.97 134.94 2
0 0 -16 1118.95 233.654 2
0 1 1 -1.12013 4.33256 1
0 -1 -1 11579.3 259.682 1
0 1 2 -5.82787 11.4471 1
0 1 -2 2.88045 3.62504 2
0 -1 2 36.4157 10.6138 2
0 -1 -2 52.9081 25.4848 1
0 1 -3 1250.47 84.4598 2
0 1 3 1444.31 122.909 1
0 1 -4 5246 211.861 2
0 1 -4 5251.2 208.618 1
0 1 4 5493.57 264.222 1
0 1 5 15.6669 26.0178 1
0 1 -5 21.5501 12.6774 1
0 -1 -5 -13.8432 19.9251 1
0 1 -5 -6.17482 28.8887 2
0 1 6 24371.8 662.342 1
0 1 -6 23681.6 582.584 1
0 1 -6 24992.8 610.037 2
0 -1 -6 23551.3 691.928 1
0 1 -7 15434.7 526.767 1
0 1 -7 15182.3 511.307 2
0 1 -8 16486.1 585.828 1
0 1 -8 16825.8 572.212 2
0 1 -9 9753.73 460.606 2
0 -1 -10 306.186 109.954 2
0 1 -10 387.194 91.4757 2
0 -1 -11 3133.22 320.116 2
0 1 -11 4013.49 332.208 2
0 -1 -12 1405.89 228.089 2
0 1 -12 1196.51 205.951 2
0 -1 -13 1088.7 214.161 2
0 1 -13 736.127 161.264 2
0 1 -14 80.4491 79.7682 2
0 -1 -14 45.4546 93.392 2
0 1 -15 1778.67 272.141 2
0 -1 -15 1968.34 309.461 2
0 -1 -16 1292.5 265.413 2
0 -1 -17 7963.66 667.891 2
0 2 0 7.38317 5.28955 1
0 2 1 -0.75608 6.0722 1
0 2 -1 81025.3 655.643 1
0 2 -2 49229.4 488.829 1
0 -2 2 49284.6 479.727 1
0 -2 -2 51314.9 777.72 1
0 2 2 49935.6 737.107 1
0 -2 3 31493.5 407.417 2
0 -2 -3 33155.4 693.112 1
0 2 3 31522.8 641.382 1
0 2 -4 1137.75 87.9495 2
0 -2 4 1274.8 95.1096 2
0 2 4 1086.53 131.041 1
0 2 -5 50181.9 675.632 2
0 2 5 50420.1 953.955 1
0 2 -6 46.4803 24.2229 1
0 2 -6 46.9198 24.3277 2
0 2 6 79.401 45.4825 1
0 -2 -6 -24.7053 32.6725 1
0 2 7 6470.37 386.682 1
0 2 -7 5997.35 296.327 2
0 2 -7 6706.43 319.79 1
0 2 8 19091.9 711.732 1
0 2 -8 18452.5 570.874 2
0 2 -8 17452.8 568.005 1
0 2 -9 27356.6 772.605 1
0 2 -9 28814.9 765.276 2
0 2 -10 20901.6 694.885 2
0 2 -11 18.472 58.9769 2
0 -2 -11 142.575 77.8401 2
0 -2 -12 114.333 85.0892 2
0 2 -12 29.8904 34.3227 2
0 2 -13 135.49 86.3087 2
0 -2 -13 49.513 36.1561 2
0 -2 -14 4537.95 462.979 2
0 2 -14 4208.7 381.925 2
0 2 -15 384.178 134.887 2
0 -2 -15 470.294 165.398 2
0 -2 -16 796.526 210.988 2
0 -2 -17 85.0203 68.6209 2
0 3 0 14.4747 16.8111 1
0 -3 0 23.3857 31.3429 1
0 -3 -1 20100.7 512.279 1
0 3 -1 20623.5 424.866 1
0 -3 1 21286 446.137 1
0 3 1 21368.2 508.093 1
0 3 -2 14055.5 332.536 1
0 -3 2 14343.6 325.275 1
0 3 2 14874.3 458.278 1
0 -3 -2 14044.4 466.76 1
0 3 3 4705.86 281.791 1
0 3 -3 4559.32 185.908 1
0 -3 3 4328.67 164.539 2
0 -3 -3 5126.19 304.767 1
0 3 4 2484.3 215.109 1
0 -3 4 2615.98 137.279 2
0 3 -4 2438.59 142.681 1
0 -3 -4 2589.14 231.871 1
0 3 5 32933.9 838.257 1
0 -3 5 31274.3 523.665 2
0 3 -5 31285.7 553.375 1
0 3 -6 1063.53 105.575 2
0 3 6 1415.99 185.528 1
0 3 -7 275.291 57.7809 2
0 3 -7 192.77 53.549 1
0 3 7 107.511 59.2194 1
0 3 8 3350.8 312.997 1
0 3 -8 3301.79 230.398 1
0 3 -8 3514.76 232.067 2
0 3 9 12609.6 639.595 1
0 3 -9 11596.9 475.398 1
0 3 -9 11774.3 456.759 2
0 3 -10 4210.29 295.262 2
0 3 -11 2968.52 257.984 2
0 3 -12 621.999 125.999 2
0 3 -13 1.88057 47.4481 2
0 -3 -13 61.3263 72.9935 2
0 -3 -14 303.541 157.532 2
0 3 -14 31.25 40.3312 2
0 -3 -15 1546.53 292.473 2
0 -3 -16 318.091 153.258 2
0 -3 -17 6791.07 656.549 2
0 -3 -18 1704.04 338.852 2
0 4 0 151.133 50.5267 1
0 -4 0 249.312 65.5702 1
0 4 -1 71657.1 936.592 1
0 -4 -1 72401.5 1125.73 1
0 -4 1 71322.3 954.823 1
0 4 2 171599 1744.67 1
0 -4 -2 171125 1837.59 1
0 -4 3 4035.35 198.725 1
0 -4 -3 4206.47 302.156 1
0 4 3 4109.86 285.05 1
0 4 -3 4081.01 203.102 1
0 4 -4 57470.3 741.686 1
0 4 4 55785.2 1104.04 1
0 -4 4 57225.4 682.314 2
0 4 -5 98357.8 1027.61 1
0 4 5 100959 1573.15 1
0 -4 5 100683 953.995 2
0 4 -6 29599 593.836 1
0 4 6 28012.9 872.007 1
0 -4 6 28520.6 541.114 2
0 4 -7 5649.21 279.768 1
0 4 7 5325.45 397.692 1
0 4 -8 1998.01 179.147 1
0 4 -8 2084.46 174.431 1
0 4 -9 10217.7 419.236 1
0 4 -9 8796.88 381.047 1
0 4 9 8971.89 560.948 1
0 4 -10 34208.1 838.476 1
0 4 -10 34651.7 812.542 2
0 4 10 34274.8 1150.35 1
0 4 -11 421.89 98.1495 2
0 4 -12 83.5187 50.9257 2
0 4 -13 4048.72 337.036 2
0 -4 -14 5384.46 541.263 2
0 -4 -15 5586.09 565.058 2
0 -4 -16 74.514 81.3622 2
0 -4 -17 11.339 108.845 2
0 -4 -18 177.695 166.449 2
0 -5 0 -3.5962 19.6083 1
0 5 0 7.72813 22.6611 1
0 5 1 17.4574 22.018 1
0 5 -1 2.25795 23.9516 1
0 -5 -1 72.7025 43.444 1
0 -5 1 -5.45057 30.8542 1
0 -5 2 817.055 103.802 1
0 5 -2 744.762 101.058 1
0 5 2 834.964 136.408 1
0 -5 -2 761.018 137.604 1
0 5 3 8815.46 448.793 1
0 5 -3 8567.47 327.341 1
0 -5 3 8621.23 338.553 1
0 5 4 2625.94 257.878 1
0 -5 4 2623.1 174.216 1
0 5 -4 2653.32 178.98 1
0 5 -5 206.613 53.8657 1
0 5 5 142.727 70.2442 1
0 -5 5 187.308 44.251 2
0 -5 6 317.486 60.0274 2
0 5 -6 475.122 79.9801 1
0 5 6 345.539 103.856 1
0 5 7 42026 1170.17 1
0 5 -7 42665.6 768.248 1
0 -5 7 41490.8 705.141 2
0 5 -8 5360.96 301.029 1
0 5 8 5212.38 431.883 1
0 5 9 32817.4 1125.02 1
0 5 -9 32847.9 757.336 1
0 5 -9 32494.7 708.964 1
0 5 -10 6388.75 359.626 1
0 5 10 6846 533.769 1
0 5 -11 4041.5 301.961 1
0 5 11 4721.01 468.079 1
0 5 -12 271.166 82.7547 1
0 -5 -14 -54.8842 97.385 2
0 -5 -15 6970.04 661.922 2
0 -5 -16 2037.05 362.35 2
0 -5 -17 314.844 156.81 2
0 -5 -18 2521.2 464.091 2
0 -6 0 113563 1606.86 1
0 6 0 109578 1479.8 1
0 -6 1 9366.48 446.316 1
0 6 -1 8736.83 402.322 1
0 6 1 7855.2 418.537 1
0 -6 -1 8962.11 476.97 1
0 -6 2 72025.5 1141.07 1
0 6 -2 76010 1113.87 1
0 -6 3 71598 1082.6 1
0 6 -3 71809.8 1060.46 1
0 6 3 73101.4 1377.5 1
0 6 4 4226.62 349.647 1
0 -6 4 3656.02 233.665 1
0 6 -4 3722.14 231.458 1
0 6 -5 48040 818.467 1
0 6 5 47990.9 1215.7 1
0 -6 5 46511.4 742.15 2
0 6 -6 4768.41 261.03 1
0 -6 6 4656.92 229.955 2
0 -6 7 168.849 46.8903 2
0 6 -7 132.596 38.9405 1
0 6 7 275.531 100.847 1
0 6 8 6148.18 488.339 1
0 6 -8 6273.65 304.793 1
0 6 -9 14390.9 493.186 1
0 6 9 14272.2 770.899 1
0 6 -9 14370.5 452.544 1
0 6 10 278.953 134.516 1
0 6 -10 147.273 56.213 1
0 6 -11 1392.7 166.084 1
0 6 11 1694.53 289.951 1
0 6 12 2548.31 373.305 1
0 -6 -15 239.178 145.644 2
0 -6 -16 138.755 176.318 2
0 -6 -17 2523.29 432.392 2
0 7 0 21.3303 44.5754 1
0 7 1 3112.64 279.728 1
0 -7 1 3898.8 315.038 1
0 7 -1 4004.81 288.959 1
0 7 2 671.593 131.229 1
0 7 -2 734.766 120.015 1
0 -7 2 801.644 138.975 1
0 -7 3 4607.14 310.575 1
0 7 -3 4085.14 269.134 1
0 -7 4 2198.98 199.689 1
0 7 4 2191.11 267.127 1
0 7 -4 2465.21 208.997 1
0 -7 5 4768.35 273.876 1
0 7 -5 4532.05 270.821 1
0 7 5 4615.95 395.089 1
0 -7 6 1908.59 155.746 2
0 7 -6 2222.3 187.381 1
0 7 6 2098.93 278.746 1
0 -7 7 447.607 80.5376 2
0 7 -7 298.898 72.2194 1
0 7 7 483.848 154.285 1
0 7 8 18.0097 64.1632 1
0 -7 8 123.074 48.6732 2
0 7 -8 171.298 52.1933 1
0 7 9 12779 763.596 1
0 7 -9 15082.7 527.544 1
0 7 10 231.853 134.543 1
0 7 11 74.921 49.9027 1
0 7 12 180.672 127.726 1
0 -7 -16 -26.1587 89.0899 2
0 8 0 1496.62 200.938 1
0 8 1 979.538 167.048 1
0 8 -1 878.93 145.777 1
0 8 2 2999.9 300.807 1
0 8 -2 2610.85 246.831 1
0 -8 2 2466.87 250.116 1
0 8 -3 41684.2 928.36 1
0 -8 3 39687.2 981.088 1
0 8 3 39783.4 1156.99 1
0 8 -4 1341.64 164.784 1
0 8 4 1307.77 219.468 1
0 -8 4 1075.63 165.721 1
0 -8 5 11190.7 463 1
0 8 5 12209.2 679.888 1
0 8 -5 11453.5 457.114 1
0 8 -6 3976.75 261.654 1
0 8 6 4207.48 418.87 1
0 -8 6 4399.48 261.076 2
0 8 -7 1205.43 140.743 1
0 8 7 1165.78 222.356 1
0 8 -8 4294.34 253.513 1
0 8 8 4921.54 473.432 1
0 8 9 10522.1 716.693 1
0 8 10 -40.7593 50.4219 1
0 8 11 2261.52 353.194 1
0 8 12 -48.4262 56.8443 1
0 -8 -16 527.004 226.995 2
0 9 0 22.9377 38.8537 1
0 9 -1 11524.4 566.617 1
0 9 1 11146.3 592.107 1
0 9 2 14914.7 713.627 1
0 9 -2 14036.1 604.813 1
0 9 -3 293.996 91.9757 1
0 9 3 133.4 91.8574 1
0 9 -4 10276.8 473.654 1
0 9 4 9578.6 614.654 1
0 -9 4 9606.7 503.888 1
0 9 -5 20163.7 639.108 1
0 -9 5 20133.7 674.844 1
0 9 5 20370 920.872 1
0 9 6 4763.86 471.224 1
0 9 -6 4670.44 296.746 1
0 9 7 342.052 152.19 1
0 9 -7 559.412 96.8195 1
0 9 8 4959.1 499.558 1
0 9 9 1438.96 285.392 1
0 9 10 118.707 96.9082 1
0 9 11 1765.52 324.636 1
0 9 12 469.507 192.109 1
0 9 13 108.509 152.532 1
0 10 0 1041.1 182.495 1
0 10 -1 97.2165 73.6121 1
0 10 1 -30.2276 51.8243 1
0 10 2 618.619 154.269 1
0 10 -2 491.014 127.573 1
0 10 -3 7212.54 438.215 1
0 10 3 7573.8 559.184 1
0 10 -4 903.898 151.442 1
0 10 4 552.696 152.945 1
0 10 5 2638.39 342.107 1
0 10 -5 1968.91 211.403 1
0 10 6 331.971 120.878 1
0 10 -6 233.927 68.9114 1
0 10 7 1078.63 237.845 1
0 10 8 293.028 155.253 1
0 10 9 399.324 169.579 1
0 10 10 1592.74 313.173 1
0 10 11 1900.56 350.872 1
0 10 12 2859.51 453.631 1
0 10 13 27.6015 84.1903 1
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