#------------------------------------------------------------------------------
#$Date: 2024-04-04 03:51:14 +0300 (Thu, 04 Apr 2024) $
#$Revision: 290771 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/57/13/1571359.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_1571359
loop_
_publ_author_name
'Li, Xing-Chi'
'Cheng, Ying'
'Wang, Xu-Dong'
'Tong, Shuo'
'Wang, Mei-Xiang'
_publ_section_title
;
 De novo synthesis of inherently chiral heteracalix[4]aromatics
 from enantioselective macrocyclization enabled by chiral phosphoric
 acid-catalyzed intramolecular SNAr reaction.
;
_journal_issue                   10
_journal_name_full               'Chemical science'
_journal_page_first              3610
_journal_page_last               3615
_journal_paper_doi               10.1039/d3sc06436k
_journal_volume                  15
_journal_year                    2024
_chemical_formula_moiety         'C34 H37 N9 O4'
_chemical_formula_sum            'C34 H37 N9 O4'
_chemical_formula_weight         635.72
_space_group_crystal_system      orthorhombic
_space_group_IT_number           18
_space_group_name_Hall           'P 2 2ab'
_space_group_name_H-M_alt        'P 21 21 2'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_audit_creation_date             2023-08-01
_audit_creation_method
;
Olex2 1.5
(compiled 2023.03.06 svn.rbb2c1857 for OlexSys, GUI svn.r6748)
;
_audit_update_record
;
2023-10-27 deposited with the CCDC.	2024-01-25 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   24.6160(7)
_cell_length_b                   13.0934(5)
_cell_length_c                   9.9979(3)
_cell_measurement_reflns_used    19984
_cell_measurement_temperature    99.99(10)
_cell_measurement_theta_max      76.6230
_cell_measurement_theta_min      3.3260
_cell_volume                     3222.39(18)
_computing_cell_refinement       'CrysAlisPro 1.171.42.85a (Rigaku OD, 2023)'
_computing_data_collection       'CrysAlisPro 1.171.42.85a (Rigaku OD, 2023)'
_computing_data_reduction        'CrysAlisPro 1.171.42.85a (Rigaku OD, 2023)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'olex2.solve 1.5 (Bourhis et al., 2015)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      99.99(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.988
_diffrn_measured_fraction_theta_max 0.964
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω   -118.00 -24.00   0.50    0.05    --  -46.63 -77.00  90.00  188
  2  ω   -118.00 -47.00   0.50    0.05    --  -46.63 -77.00 -30.00  142
  3  ω   -118.00 -32.00   0.50    0.05    --  -46.63 -57.00-180.00  172
  4  ω    -40.00  27.00   0.50    0.05    --  -46.63  37.00-150.00  134
  5  ω    -69.00 -29.00   0.50    0.05    -- -102.00  61.00 150.00   80
  6  ω    -69.00 -29.00   0.50    0.05    -- -102.00  61.00  60.00   80
  7  ω    -69.00 -29.00   0.50    0.05    -- -102.00  61.00 -30.00   80
  8  ω     82.00 178.00   0.50    0.05    --  104.75  77.00   0.00  192
  9  ω     91.00 178.00   0.50    0.05    --  104.75  15.00 -77.00  174
 10  ω     32.00  73.00   0.50    0.05    --  104.75 -61.00  30.00   82
 11  ω     32.00  73.00   0.50    0.05    --  104.75 -61.00   0.00   82
 12  ω     92.00 177.00   0.50    0.05    --  104.75  45.00-150.00  170
 13  ω     32.00  73.00   0.50    0.05    --  104.75 -61.00-180.00   82
 14  ω    -28.00  28.00   0.50    0.05    --   46.63 -19.00   0.00  112
 15  ω     32.00  73.00   0.50    0.05    --  104.75 -61.00  90.00   82
 16  ω     32.00 109.00   0.50    0.05    --  104.75 -94.00  30.00  154
 17  ω      7.00  85.00   0.50    0.05    --   46.63-113.00 -52.00  156
 18  ω     32.00 132.00   0.50    0.05    --  104.75-147.00-120.00  200
 19  ω     36.00 112.00   0.50    0.05    --  104.75-113.00 -52.00  152
 20  ω     35.00 117.00   0.50    0.05    --  104.75-125.00   0.00  164
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy R, DW system, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0109198000
_diffrn_orient_matrix_UB_12      0.1151992000
_diffrn_orient_matrix_UB_13      -0.0163860000
_diffrn_orient_matrix_UB_21      -0.0042007000
_diffrn_orient_matrix_UB_22      -0.0139763000
_diffrn_orient_matrix_UB_23      -0.1526239000
_diffrn_orient_matrix_UB_31      -0.0614504000
_diffrn_orient_matrix_UB_32      -0.0197450000
_diffrn_orient_matrix_UB_33      0.0134040000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0522
_diffrn_reflns_av_unetI/netI     0.0321
_diffrn_reflns_Laue_measured_fraction_full 0.988
_diffrn_reflns_Laue_measured_fraction_max 0.964
_diffrn_reflns_limit_h_max       26
_diffrn_reflns_limit_h_min       -30
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            27752
_diffrn_reflns_point_group_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.957
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         77.093
_diffrn_reflns_theta_min         3.591
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.727
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.43493
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.42.85a (Rigaku Oxford Diffraction, 2023)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_density_diffrn    1.310
_exptl_crystal_description       needle
_exptl_crystal_F_000             1344
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.181
_refine_diff_density_min         -0.235
_refine_diff_density_rms         0.049
_refine_ls_abs_structure_details
;
 Flack x determined using 2417 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.13(12)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.116
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     472
_refine_ls_number_reflns         6548
_refine_ls_number_restraints     10
_refine_ls_restrained_S_all      1.116
_refine_ls_R_factor_all          0.0468
_refine_ls_R_factor_gt           0.0420
_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/[σ²(Fo²)+(0.0541P)²+0.9332P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1057
_refine_ls_wR_factor_ref         0.1140
_reflns_Friedel_coverage         0.764
_reflns_Friedel_fraction_full    0.999
_reflns_Friedel_fraction_max     0.948
_reflns_number_gt                6031
_reflns_number_total             6548
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d3sc06436k2.cif
_cod_data_source_block           exp_16702_auto
_cod_database_code               1571359
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         CHONCl
_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_estimated_absorpt_t_max   0.965
_shelx_estimated_absorpt_t_min   0.899
_olex2_refinement_description
;
1. Restrained distances
 C00Q-C015 \\sim C00Q-C0
 with sigma of 0.02
 C015-C019 \\sim C0-C3
 with sigma of 0.02
 C015-C1 \\sim C0-C1A
 with sigma of 0.02
 C015-C2 \\sim C0-C2A
 with sigma of 0.02
 C00Q-C019 \\sim C00Q-C3
 with sigma of 0.04
 C00Q-C1 \\sim C00Q-C1A
 with sigma of 0.04
 C00Q-C2 \\sim C00Q-C2A
 with sigma of 0.04
 C019-C1 \\sim C3-C1A
 with sigma of 0.04
 C019-C2 \\sim C3-C2A
 with sigma of 0.04
 C1-C2 \\sim C1A-C2A
 with sigma of 0.04
2. Others
 Sof(C2A)=Sof(H2AA)=Sof(H2AB)=Sof(H2AC)=Sof(C0)=Sof(C3)=Sof(H3A)=Sof(H3B)=
 Sof(H3C)=Sof(C1A)=Sof(H1AA)=Sof(H1AB)=Sof(H1AC)=1-FVAR(1)
 Sof(C015)=Sof(C019)=Sof(H01J)=Sof(H01K)=Sof(H01L)=Sof(C1)=Sof(H1A)=Sof(H1B)=
 Sof(H1C)=Sof(C2)=Sof(H2A)=Sof(H2B)=Sof(H2C)=FVAR(1)
3.a Secondary CH2 refined with riding coordinates:
 C00X(H00G,H00H)
3.b Aromatic/amide H refined with riding coordinates:
 C00O(H00O), C00R(H00R), C00S(H00S), C00T(H00T), C00U(H00U), C00Y(H00Y),
 C00Z(H00Z), C011(H011), C013(H013), C014(H014), C017(H017)
3.c Idealised Me refined as rotating group:
 C00V(H00A,H00B,H00C), C00W(H00D,H00E,H00F), C012(H01A,H01B,H01C), C016(H01D,
 H01E,H01F), C018(H01G,H01H,H01I), C019(H01J,H01K,H01L), C1(H1A,H1B,H1C),
 C2(H2A,H2B,H2C), C2A(H2AA,H2AB,H2AC), C3(H3A,H3B,H3C), C1A(H1AA,H1AB,H1AC)
;
_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 2.634
_oxdiff_exptl_absorpt_empirical_full_min 0.571
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, z'
'-x+1/2, y+1/2, -z'
'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
O001 O 0.33358(8) 0.64575(15) 0.71784(19) 0.0323(4) Uani 1 1 d . . . . .
O002 O 0.43929(8) 0.73734(16) 0.2879(2) 0.0339(4) Uani 1 1 d . . . . .
O003 O 0.39663(10) 0.95970(16) 0.8241(2) 0.0393(5) Uani 1 1 d . . . . .
O004 O 0.45797(8) 0.25922(15) 0.0614(2) 0.0351(4) Uani 1 1 d . . . . .
N005 N 0.37607(9) 0.47795(18) 0.2539(2) 0.0303(5) Uani 1 1 d . . . . .
N006 N 0.40639(9) 0.30446(18) 0.2431(2) 0.0299(5) Uani 1 1 d . . . . .
N007 N 0.38256(9) 0.92463(18) 0.6079(2) 0.0286(5) Uani 1 1 d . . . . .
N008 N 0.43297(9) 0.42228(18) 0.0728(2) 0.0301(5) Uani 1 1 d . . . . .
N009 N 0.36691(10) 0.88034(18) 0.3872(2) 0.0312(5) Uani 1 1 d . . . . .
N00A N 0.34921(10) 0.36106(18) 0.4110(2) 0.0326(5) Uani 1 1 d . . . . .
N00B N 0.40556(9) 0.59006(18) 0.0917(2) 0.0295(5) Uani 1 1 d . . . . .
N00C N 0.36536(10) 0.79938(18) 0.7763(2) 0.0313(5) Uani 1 1 d . . . . .
N00D N 0.34875(9) 0.75944(18) 0.5473(2) 0.0275(5) Uani 1 1 d . . . . .
C00E C 0.40462(10) 0.4939(2) 0.1407(3) 0.0280(6) Uani 1 1 d . . . . .
C00F C 0.37831(11) 0.3823(2) 0.2989(3) 0.0294(6) Uani 1 1 d . . . . .
C00G C 0.31047(11) 0.5822(2) 0.6206(3) 0.0288(6) Uani 1 1 d . . . . .
C00H C 0.36645(10) 0.8549(2) 0.5175(3) 0.0265(5) Uani 1 1 d . . . . .
C00I C 0.43111(11) 0.3314(2) 0.1313(3) 0.0293(6) Uani 1 1 d . . . . .
C00J C 0.34989(10) 0.7395(2) 0.6766(3) 0.0272(5) Uani 1 1 d . . . . .
C00K C 0.35013(11) 0.8084(2) 0.2875(3) 0.0293(6) Uani 1 1 d . . . . .
C00L C 0.38102(11) 0.8910(2) 0.7336(3) 0.0290(6) Uani 1 1 d . . . . .
C00M C 0.31794(11) 0.4413(2) 0.4711(3) 0.0295(6) Uani 1 1 d . . . . .
C00N C 0.38648(10) 0.7349(2) 0.2418(3) 0.0281(5) Uani 1 1 d . . . . .
C00O C 0.29844(11) 0.8159(2) 0.2330(3) 0.0311(6) Uani 1 1 d . . . . .
H00O H 0.274376 0.867117 0.265029 0.037 Uiso 1 1 calc R U . . .
C00P C 0.36931(11) 0.6661(2) 0.1442(3) 0.0280(6) Uani 1 1 d . . . . .
C00Q C 0.28109(11) 0.7498(2) 0.1322(3) 0.0320(6) Uani 1 1 d D . . . .
C00R C 0.34116(11) 0.5041(2) 0.5681(3) 0.0299(6) Uani 1 1 d . . . . .
H00R H 0.377406 0.493128 0.597377 0.036 Uiso 1 1 calc R U . . .
C00S C 0.26476(12) 0.4567(2) 0.4311(3) 0.0342(6) Uani 1 1 d . . . . .
H00S H 0.249024 0.413544 0.365177 0.041 Uiso 1 1 calc R U . . .
C00T C 0.25723(12) 0.5978(2) 0.5832(3) 0.0333(6) Uani 1 1 d . . . . .
H00T H 0.236463 0.650977 0.622864 0.040 Uiso 1 1 calc R U . . .
C00U C 0.31749(11) 0.6748(2) 0.0907(3) 0.0309(6) Uani 1 1 d . . . . .
H00U H 0.306466 0.627938 0.023441 0.037 Uiso 1 1 calc R U . . .
C00V C 0.43289(12) 0.6119(2) -0.0353(3) 0.0346(6) Uani 1 1 d . . . . .
H00A H 0.469522 0.582621 -0.033837 0.052 Uiso 1 1 calc R U . . .
H00B H 0.435322 0.686008 -0.047932 0.052 Uiso 1 1 calc R U . . .
H00C H 0.412125 0.581785 -0.109000 0.052 Uiso 1 1 calc R U . . .
C00W C 0.38921(13) 0.9772(2) 0.3395(3) 0.0370(7) Uani 1 1 d . . . . .
H00D H 0.399343 1.019724 0.416194 0.056 Uiso 1 1 calc R U . . .
H00E H 0.361823 1.012806 0.285789 0.056 Uiso 1 1 calc R U . . .
H00F H 0.421412 0.963947 0.284538 0.056 Uiso 1 1 calc R U . . .
C00X C 0.45455(12) 0.6617(2) 0.3848(3) 0.0353(6) Uani 1 1 d . . . . .
H00G H 0.479204 0.611253 0.342885 0.042 Uiso 1 1 calc R U . . .
H00H H 0.421740 0.624996 0.416078 0.042 Uiso 1 1 calc R U . . .
C00Y C 0.23446(11) 0.5349(2) 0.4871(3) 0.0358(6) Uani 1 1 d . . . . .
H00Y H 0.197956 0.545417 0.459467 0.043 Uiso 1 1 calc R U . . .
C00Z C 0.52418(13) 0.8544(3) 0.6168(3) 0.0455(8) Uani 1 1 d . . . . .
H00Z H 0.533915 0.924613 0.616940 0.055 Uiso 1 1 calc R U . . .
C010 C 0.48271(11) 0.7110(2) 0.5030(3) 0.0326(6) Uani 1 1 d . . . . .
C011 C 0.49760(12) 0.8127(2) 0.5059(3) 0.0359(6) Uani 1 1 d . . . . .
H011 H 0.489662 0.855010 0.431190 0.043 Uiso 1 1 calc R U . . .
C012 C 0.45928(13) 0.1589(2) 0.1180(3) 0.0390(7) Uani 1 1 d . . . . .
H01A H 0.476610 0.111752 0.054960 0.059 Uiso 1 1 calc R U . . .
H01B H 0.422104 0.135975 0.136232 0.059 Uiso 1 1 calc R U . . .
H01C H 0.480018 0.160187 0.201683 0.059 Uiso 1 1 calc R U . . .
C013 C 0.49469(13) 0.6517(3) 0.6142(3) 0.0483(8) Uani 1 1 d . . . . .
H013 H 0.484350 0.581770 0.615376 0.058 Uiso 1 1 calc R U . . .
C014 C 0.52178(14) 0.6933(4) 0.7247(3) 0.0546(10) Uani 1 1 d . . . . .
H014 H 0.530187 0.651319 0.799446 0.066 Uiso 1 1 calc R U . . .
C015 C 0.2232(4) 0.7568(11) 0.0738(13) 0.042(4) Uani 0.598(8) 1 d D . P A 1
C016 C 0.35579(13) 0.2670(2) 0.4855(3) 0.0380(7) Uani 1 1 d . . . . .
H01D H 0.365883 0.211853 0.424089 0.057 Uiso 1 1 calc R U . . .
H01E H 0.321539 0.249810 0.530060 0.057 Uiso 1 1 calc R U . . .
H01F H 0.384398 0.275792 0.552666 0.057 Uiso 1 1 calc R U . . .
C017 C 0.53623(12) 0.7947(3) 0.7252(3) 0.0486(9) Uani 1 1 d . . . . .
H017 H 0.554449 0.823173 0.800174 0.058 Uiso 1 1 calc R U . . .
C018 C 0.39453(19) 0.9264(3) 0.9611(3) 0.0553(10) Uani 1 1 d . . . . .
H01G H 0.421685 0.872825 0.975573 0.083 Uiso 1 1 calc R U . . .
H01H H 0.358271 0.899461 0.980777 0.083 Uiso 1 1 calc R U . . .
H01I H 0.402218 0.984347 1.020218 0.083 Uiso 1 1 calc R U . . .
C019 C 0.1909(2) 0.8476(6) 0.1279(7) 0.056(2) Uani 0.598(8) 1 d D . P A 1
H01J H 0.186236 0.840167 0.224714 0.085 Uiso 0.598(8) 1 calc R U P A 1
H01K H 0.155206 0.849779 0.084620 0.085 Uiso 0.598(8) 1 calc R U P A 1
H01L H 0.210591 0.911039 0.108907 0.085 Uiso 0.598(8) 1 calc R U P A 1
C1 C 0.2287(3) 0.7679(10) -0.0779(6) 0.079(3) Uani 0.598(8) 1 d D . P A 1
H1A H 0.247736 0.831693 -0.098746 0.118 Uiso 0.598(8) 1 calc R U P A 1
H1B H 0.192511 0.769021 -0.118679 0.118 Uiso 0.598(8) 1 calc R U P A 1
H1C H 0.249415 0.710038 -0.113611 0.118 Uiso 0.598(8) 1 calc R U P A 1
C2 C 0.1917(3) 0.6606(6) 0.1077(10) 0.072(3) Uani 0.598(8) 1 d D . P A 1
H2A H 0.210443 0.601072 0.070272 0.109 Uiso 0.598(8) 1 calc R U P A 1
H2B H 0.155074 0.665123 0.069554 0.109 Uiso 0.598(8) 1 calc R U P A 1
H2C H 0.189133 0.653455 0.205039 0.109 Uiso 0.598(8) 1 calc R U P A 1
C2A C 0.1817(3) 0.7626(10) 0.1608(10) 0.057(3) Uani 0.402(8) 1 d D . P A 2
H2AA H 0.181479 0.695942 0.205266 0.085 Uiso 0.402(8) 1 calc R U P A 2
H2AB H 0.146665 0.773656 0.116293 0.085 Uiso 0.402(8) 1 calc R U P A 2
H2AC H 0.187613 0.816455 0.227269 0.085 Uiso 0.402(8) 1 calc R U P A 2
C0 C 0.2272(7) 0.7655(13) 0.0571(19) 0.037(5) Uani 0.402(8) 1 d D . P A 2
C3 C 0.2278(4) 0.8688(9) -0.0128(12) 0.069(4) Uani 0.402(8) 1 d D . P A 2
H3A H 0.239853 0.921444 0.050278 0.104 Uiso 0.402(8) 1 calc R U P A 2
H3B H 0.191156 0.885141 -0.044514 0.104 Uiso 0.402(8) 1 calc R U P A 2
H3C H 0.252801 0.866302 -0.088970 0.104 Uiso 0.402(8) 1 calc R U P A 2
C1A C 0.2160(4) 0.6801(11) -0.0452(12) 0.067(4) Uani 0.402(8) 1 d D . P A 2
H1AA H 0.245868 0.677182 -0.109986 0.100 Uiso 0.402(8) 1 calc R U P A 2
H1AB H 0.181901 0.694254 -0.092164 0.100 Uiso 0.402(8) 1 calc R U P A 2
H1AC H 0.213214 0.614459 0.001415 0.100 Uiso 0.402(8) 1 calc R U P A 2
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
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C00J O001 C00G 116.5(2) . . ?
C00N O002 C00X 117.1(2) . . ?
C00L O003 C018 115.6(2) . . ?
C00I O004 C012 116.7(2) . . ?
C00F N005 C00E 114.0(2) . . ?
C00I N006 C00F 112.6(2) . . ?
C00L N007 C00H 113.7(2) . . ?
C00I N008 C00E 112.5(2) . . ?
C00H N009 C00K 120.6(2) . . ?
C00H N009 C00W 122.3(2) . . ?
C00K N009 C00W 116.8(2) . . ?
C00F N00A C00M 118.5(2) . . ?
C00F N00A C016 122.6(2) . . ?
C00M N00A C016 117.9(2) . . ?
C00E N00B C00P 120.2(2) . . ?
C00E N00B C00V 120.3(2) . . ?
C00P N00B C00V 117.8(2) . . ?
C00J N00C C00L 112.0(2) . . ?
C00J N00D C00H 113.0(2) . . ?
N005 C00E N008 125.7(3) . . ?
N005 C00E N00B 117.2(2) . . ?
N00B C00E N008 117.1(2) . . ?
N005 C00F N006 126.2(3) . . ?
N005 C00F N00A 116.7(2) . . ?
N006 C00F N00A 117.1(2) . . ?
C00R C00G O001 118.9(2) . . ?
C00R C00G C00T 121.9(3) . . ?
C00T C00G O001 119.1(3) . . ?
N007 C00H N009 118.7(2) . . ?
N007 C00H N00D 125.0(2) . . ?
N009 C00H N00D 116.3(2) . . ?
N006 C00I O004 118.6(2) . . ?
N006 C00I N008 128.9(3) . . ?
N008 C00I O004 112.5(2) . . ?
N00C C00J O001 113.0(2) . . ?
N00D C00J O001 118.1(2) . . ?
N00D C00J N00C 128.9(3) . . ?
C00N C00K N009 119.9(2) . . ?
C00O C00K N009 119.4(3) . . ?
C00O C00K C00N 120.7(3) . . ?
N007 C00L O003 114.1(2) . . ?
N00C C00L O003 118.3(2) . . ?
N00C C00L N007 127.5(3) . . ?
C00R C00M N00A 120.2(3) . . ?
C00S C00M N00A 119.5(3) . . ?
C00S C00M C00R 120.2(3) . . ?
O002 C00N C00K 118.7(2) . . ?
O002 C00N C00P 122.3(2) . . ?
C00K C00N C00P 118.8(2) . . ?
C00K C00O H00O 119.3 . . ?
C00K C00O C00Q 121.3(3) . . ?
C00Q C00O H00O 119.3 . . ?
C00N C00P N00B 121.1(2) . . ?
C00U C00P N00B 119.2(3) . . ?
C00U C00P C00N 119.7(3) . . ?
C00O C00Q C015 121.3(6) . . ?
C00O C00Q C0 122.3(7) . . ?
C00U C00Q C00O 117.1(3) . . ?
C00U C00Q C015 121.6(6) . . ?
C00U C00Q C0 120.3(7) . . ?
C00G C00R C00M 118.6(3) . . ?
C00G C00R H00R 120.7 . . ?
C00M C00R H00R 120.7 . . ?
C00M C00S H00S 120.0 . . ?
C00M C00S C00Y 120.0(3) . . ?
C00Y C00S H00S 120.0 . . ?
C00G C00T H00T 120.5 . . ?
C00G C00T C00Y 119.0(3) . . ?
C00Y C00T H00T 120.5 . . ?
C00P C00U C00Q 122.3(3) . . ?
C00P C00U H00U 118.8 . . ?
C00Q C00U H00U 118.8 . . ?
N00B C00V H00A 109.5 . . ?
N00B C00V H00B 109.5 . . ?
N00B C00V H00C 109.5 . . ?
H00A C00V H00B 109.5 . . ?
H00A C00V H00C 109.5 . . ?
H00B C00V H00C 109.5 . . ?
N009 C00W H00D 109.5 . . ?
N009 C00W H00E 109.5 . . ?
N009 C00W H00F 109.5 . . ?
H00D C00W H00E 109.5 . . ?
H00D C00W H00F 109.5 . . ?
H00E C00W H00F 109.5 . . ?
O002 C00X H00G 109.5 . . ?
O002 C00X H00H 109.5 . . ?
O002 C00X C010 110.6(2) . . ?
H00G C00X H00H 108.1 . . ?
C010 C00X H00G 109.5 . . ?
C010 C00X H00H 109.5 . . ?
C00S C00Y H00Y 119.9 . . ?
C00T C00Y C00S 120.2(3) . . ?
C00T C00Y H00Y 119.9 . . ?
C011 C00Z H00Z 119.8 . . ?
C017 C00Z H00Z 119.8 . . ?
C017 C00Z C011 120.4(3) . . ?
C011 C010 C00X 123.3(3) . . ?
C011 C010 C013 117.8(3) . . ?
C013 C010 C00X 118.9(3) . . ?
C00Z C011 H011 119.4 . . ?
C010 C011 C00Z 121.1(3) . . ?
C010 C011 H011 119.4 . . ?
O004 C012 H01A 109.5 . . ?
O004 C012 H01B 109.5 . . ?
O004 C012 H01C 109.5 . . ?
H01A C012 H01B 109.5 . . ?
H01A C012 H01C 109.5 . . ?
H01B C012 H01C 109.5 . . ?
C010 C013 H013 119.5 . . ?
C010 C013 C014 121.0(3) . . ?
C014 C013 H013 119.5 . . ?
C013 C014 H014 120.0 . . ?
C017 C014 C013 120.1(3) . . ?
C017 C014 H014 120.0 . . ?
C019 C015 C00Q 113.1(8) . . ?
C019 C015 C1 108.8(10) . . ?
C1 C015 C00Q 107.4(8) . . ?
C2 C015 C00Q 109.8(8) . . ?
C2 C015 C019 107.4(9) . . ?
C2 C015 C1 110.2(10) . . ?
N00A C016 H01D 109.5 . . ?
N00A C016 H01E 109.5 . . ?
N00A C016 H01F 109.5 . . ?
H01D C016 H01E 109.5 . . ?
H01D C016 H01F 109.5 . . ?
H01E C016 H01F 109.5 . . ?
C00Z C017 C014 119.5(3) . . ?
C00Z C017 H017 120.2 . . ?
C014 C017 H017 120.2 . . ?
O003 C018 H01G 109.5 . . ?
O003 C018 H01H 109.5 . . ?
O003 C018 H01I 109.5 . . ?
H01G C018 H01H 109.5 . . ?
H01G C018 H01I 109.5 . . ?
H01H C018 H01I 109.5 . . ?
C015 C019 H01J 109.5 . . ?
C015 C019 H01K 109.5 . . ?
C015 C019 H01L 109.5 . . ?
H01J C019 H01K 109.5 . . ?
H01J C019 H01L 109.5 . . ?
H01K C019 H01L 109.5 . . ?
C015 C1 H1A 109.5 . . ?
C015 C1 H1B 109.5 . . ?
C015 C1 H1C 109.5 . . ?
H1A C1 H1B 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
C015 C2 H2A 109.5 . . ?
C015 C2 H2B 109.5 . . ?
C015 C2 H2C 109.5 . . ?
H2A C2 H2B 109.5 . . ?
H2A C2 H2C 109.5 . . ?
H2B C2 H2C 109.5 . . ?
H2AA C2A H2AB 109.5 . . ?
H2AA C2A H2AC 109.5 . . ?
H2AB C2A H2AC 109.5 . . ?
C0 C2A H2AA 109.5 . . ?
C0 C2A H2AB 109.5 . . ?
C0 C2A H2AC 109.5 . . ?
C00Q C0 C1A 112.4(11) . . ?
C2A C0 C00Q 107.4(12) . . ?
C2A C0 C1A 107.6(12) . . ?
C3 C0 C00Q 109.5(11) . . ?
C3 C0 C2A 109.9(12) . . ?
C3 C0 C1A 110.0(14) . . ?
C0 C3 H3A 109.5 . . ?
C0 C3 H3B 109.5 . . ?
C0 C3 H3C 109.5 . . ?
H3A C3 H3B 109.5 . . ?
H3A C3 H3C 109.5 . . ?
H3B C3 H3C 109.5 . . ?
C0 C1A H1AA 109.5 . . ?
C0 C1A H1AB 109.5 . . ?
C0 C1A H1AC 109.5 . . ?
H1AA C1A H1AB 109.5 . . ?
H1AA C1A H1AC 109.5 . . ?
H1AB C1A H1AC 109.5 . . ?
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
O001 C00G 1.400(3) . ?
O001 C00J 1.356(3) . ?
O002 C00N 1.380(3) . ?
O002 C00X 1.436(3) . ?
O003 C00L 1.332(3) . ?
O003 C018 1.438(4) . ?
O004 C00I 1.348(3) . ?
O004 C012 1.431(4) . ?
N005 C00E 1.349(3) . ?
N005 C00F 1.331(4) . ?
N006 C00F 1.352(4) . ?
N006 C00I 1.320(4) . ?
N007 C00H 1.345(3) . ?
N007 C00L 1.332(3) . ?
N008 C00E 1.352(4) . ?
N008 C00I 1.327(4) . ?
N009 C00H 1.345(3) . ?
N009 C00K 1.433(4) . ?
N009 C00W 1.462(4) . ?
N00A C00F 1.359(4) . ?
N00A C00M 1.434(4) . ?
N00A C016 1.448(4) . ?
N00B C00E 1.351(4) . ?
N00B C00P 1.436(4) . ?
N00B C00V 1.465(3) . ?
N00C C00J 1.324(4) . ?
N00C C00L 1.330(4) . ?
N00D C00H 1.356(3) . ?
N00D C00J 1.319(3) . ?
C00G C00R 1.376(4) . ?
C00G C00T 1.378(4) . ?
C00K C00N 1.391(4) . ?
C00K C00O 1.387(4) . ?
C00M C00R 1.394(4) . ?
C00M C00S 1.384(4) . ?
C00N C00P 1.394(4) . ?
C00O H00O 0.9500 . ?
C00O C00Q 1.396(4) . ?
C00P C00U 1.388(4) . ?
C00Q C00U 1.393(4) . ?
C00Q C015 1.542(10) . ?
C00Q C0 1.539(16) . ?
C00R H00R 0.9500 . ?
C00S H00S 0.9500 . ?
C00S C00Y 1.386(4) . ?
C00T H00T 0.9500 . ?
C00T C00Y 1.385(4) . ?
C00U H00U 0.9500 . ?
C00V H00A 0.9800 . ?
C00V H00B 0.9800 . ?
C00V H00C 0.9800 . ?
C00W H00D 0.9800 . ?
C00W H00E 0.9800 . ?
C00W H00F 0.9800 . ?
C00X H00G 0.9900 . ?
C00X H00H 0.9900 . ?
C00X C010 1.515(4) . ?
C00Y H00Y 0.9500 . ?
C00Z H00Z 0.9500 . ?
C00Z C011 1.399(4) . ?
C00Z C017 1.368(5) . ?
C010 C011 1.381(4) . ?
C010 C013 1.388(4) . ?
C011 H011 0.9500 . ?
C012 H01A 0.9800 . ?
C012 H01B 0.9800 . ?
C012 H01C 0.9800 . ?
C013 H013 0.9500 . ?
C013 C014 1.401(5) . ?
C014 H014 0.9500 . ?
C014 C017 1.375(6) . ?
C015 C019 1.529(14) . ?
C015 C1 1.530(14) . ?
C015 C2 1.519(15) . ?
C016 H01D 0.9800 . ?
C016 H01E 0.9800 . ?
C016 H01F 0.9800 . ?
C017 H017 0.9500 . ?
C018 H01G 0.9800 . ?
C018 H01H 0.9800 . ?
C018 H01I 0.9800 . ?
C019 H01J 0.9800 . ?
C019 H01K 0.9800 . ?
C019 H01L 0.9800 . ?
C1 H1A 0.9800 . ?
C1 H1B 0.9800 . ?
C1 H1C 0.9800 . ?
C2 H2A 0.9800 . ?
C2 H2B 0.9800 . ?
C2 H2C 0.9800 . ?
C2A H2AA 0.9800 . ?
C2A H2AB 0.9800 . ?
C2A H2AC 0.9800 . ?
C2A C0 1.53(2) . ?
C0 C3 1.522(18) . ?
C0 C1A 1.540(17) . ?
C3 H3A 0.9800 . ?
C3 H3B 0.9800 . ?
C3 H3C 0.9800 . ?
C1A H1AA 0.9800 . ?
C1A H1AB 0.9800 . ?
C1A H1AC 0.9800 . ?
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
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O001 C00G C00R C00M -179.8(2) . . . . ?
O001 C00G C00T C00Y -180.0(3) . . . . ?
O002 C00N C00P N00B 3.3(4) . . . . ?
O002 C00N C00P C00U -172.6(2) . . . . ?
O002 C00X C010 C011 -8.0(4) . . . . ?
O002 C00X C010 C013 172.4(3) . . . . ?
N009 C00K C00N O002 -4.1(4) . . . . ?
N009 C00K C00N C00P -179.7(2) . . . . ?
N009 C00K C00O C00Q 177.6(2) . . . . ?
N00A C00M C00R C00G 178.1(2) . . . . ?
N00A C00M C00S C00Y -179.1(3) . . . . ?
N00B C00P C00U C00Q -176.9(2) . . . . ?
C00E N005 C00F N006 1.0(4) . . . . ?
C00E N005 C00F N00A -178.4(2) . . . . ?
C00E N008 C00I O004 178.1(2) . . . . ?
C00E N008 C00I N006 -0.6(4) . . . . ?
C00E N00B C00P C00N 97.4(3) . . . . ?
C00E N00B C00P C00U -86.7(3) . . . . ?
C00F N005 C00E N008 1.2(4) . . . . ?
C00F N005 C00E N00B -178.0(2) . . . . ?
C00F N006 C00I O004 -176.2(2) . . . . ?
C00F N006 C00I N008 2.4(4) . . . . ?
C00F N00A C00M C00R -89.7(3) . . . . ?
C00F N00A C00M C00S 89.6(3) . . . . ?
C00G O001 C00J N00C 172.6(2) . . . . ?
C00G O001 C00J N00D -7.7(3) . . . . ?
C00G C00T C00Y C00S 0.9(4) . . . . ?
C00H N007 C00L O003 -179.7(2) . . . . ?
C00H N007 C00L N00C -0.6(4) . . . . ?
C00H N009 C00K C00N -82.2(3) . . . . ?
C00H N009 C00K C00O 100.8(3) . . . . ?
C00H N00D C00J O001 -179.3(2) . . . . ?
C00H N00D C00J N00C 0.4(4) . . . . ?
C00I N006 C00F N005 -2.6(4) . . . . ?
C00I N006 C00F N00A 176.8(2) . . . . ?
C00I N008 C00E N005 -1.4(4) . . . . ?
C00I N008 C00E N00B 177.8(2) . . . . ?
C00J O001 C00G C00R 103.2(3) . . . . ?
C00J O001 C00G C00T -78.7(3) . . . . ?
C00J N00C C00L O003 178.7(2) . . . . ?
C00J N00C C00L N007 -0.4(4) . . . . ?
C00J N00D C00H N007 -1.5(4) . . . . ?
C00J N00D C00H N009 179.4(2) . . . . ?
C00K N009 C00H N007 179.9(2) . . . . ?
C00K N009 C00H N00D -0.9(4) . . . . ?
C00K C00N C00P N00B 178.7(2) . . . . ?
C00K C00N C00P C00U 2.8(4) . . . . ?
C00K C00O C00Q C00U 1.3(4) . . . . ?
C00K C00O C00Q C015 178.7(7) . . . . ?
C00K C00O C00Q C0 -171.5(9) . . . . ?
C00L N007 C00H N009 -179.3(2) . . . . ?
C00L N007 C00H N00D 1.6(4) . . . . ?
C00L N00C C00J O001 -179.8(2) . . . . ?
C00L N00C C00J N00D 0.5(4) . . . . ?
C00M N00A C00F N005 0.9(4) . . . . ?
C00M N00A C00F N006 -178.6(2) . . . . ?
C00M C00S C00Y C00T -0.1(5) . . . . ?
C00N O002 C00X C010 -130.5(2) . . . . ?
C00N C00K C00O C00Q 0.7(4) . . . . ?
C00N C00P C00U C00Q -0.8(4) . . . . ?
C00O C00K C00N O002 172.9(2) . . . . ?
C00O C00K C00N C00P -2.7(4) . . . . ?
C00O C00Q C00U C00P -1.2(4) . . . . ?
C00O C00Q C015 C019 5.5(12) . . . . ?
C00O C00Q C015 C1 125.6(9) . . . . ?
C00O C00Q C015 C2 -114.5(8) . . . . ?
C00O C00Q C0 C2A -59.5(13) . . . . ?
C00O C00Q C0 C3 59.8(15) . . . . ?
C00O C00Q C0 C1A -177.6(9) . . . . ?
C00P N00B C00E N005 -11.5(4) . . . . ?
C00P N00B C00E N008 169.3(2) . . . . ?
C00R C00G C00T C00Y -2.0(4) . . . . ?
C00R C00M C00S C00Y 0.3(4) . . . . ?
C00S C00M C00R C00G -1.3(4) . . . . ?
C00T C00G C00R C00M 2.2(4) . . . . ?
C00U C00Q C015 C019 -177.2(6) . . . . ?
C00U C00Q C015 C1 -57.1(12) . . . . ?
C00U C00Q C015 C2 62.8(10) . . . . ?
C00U C00Q C0 C2A 127.9(9) . . . . ?
C00U C00Q C0 C3 -112.8(10) . . . . ?
C00U C00Q C0 C1A 9.8(17) . . . . ?
C00V N00B C00E N005 -176.2(2) . . . . ?
C00V N00B C00E N008 4.6(4) . . . . ?
C00V N00B C00P C00N -97.6(3) . . . . ?
C00V N00B C00P C00U 78.4(3) . . . . ?
C00W N009 C00H N007 6.1(4) . . . . ?
C00W N009 C00H N00D -174.7(2) . . . . ?
C00W N009 C00K C00N 92.0(3) . . . . ?
C00W N009 C00K C00O -85.1(3) . . . . ?
C00X O002 C00N C00K 105.2(3) . . . . ?
C00X O002 C00N C00P -79.4(3) . . . . ?
C00X C010 C011 C00Z -179.2(3) . . . . ?
C00X C010 C013 C014 178.6(3) . . . . ?
C010 C013 C014 C017 1.0(5) . . . . ?
C011 C00Z C017 C014 -0.3(5) . . . . ?
C011 C010 C013 C014 -1.0(5) . . . . ?
C012 O004 C00I N006 -2.5(4) . . . . ?
C012 O004 C00I N008 178.7(2) . . . . ?
C013 C010 C011 C00Z 0.4(4) . . . . ?
C013 C014 C017 C00Z -0.3(5) . . . . ?
C015 C00Q C00U C00P -178.6(7) . . . . ?
C016 N00A C00F N005 -167.9(3) . . . . ?
C016 N00A C00F N006 12.6(4) . . . . ?
C016 N00A C00M C00R 79.6(3) . . . . ?
C016 N00A C00M C00S -101.0(3) . . . . ?
C017 C00Z C011 C010 0.3(5) . . . . ?
C018 O003 C00L N007 178.9(3) . . . . ?
C018 O003 C00L N00C -0.2(4) . . . . ?
C0 C00Q C00U C00P 171.8(9) . . . . ?
