#------------------------------------------------------------------------------
#$Date: 2020-05-27 02:25:01 +0300 (Wed, 27 May 2020) $
#$Revision: 252364 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/03/84/4038411.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_4038411
loop_
_publ_author_name
'Castillo, Juan-Carlos'
'Castro-Agudelo, Brian'
'Gálvez, Jaime'
'Carissan, Yannick'
'Rodríguez, Jean'
'Coquerel, Yoann'
_publ_section_title
;
 Periselectivity in the aza-Diels-Alder cycloaddition between
 α-oxoketenes and N-(5-pyrazolyl)imines: a combined experimental and
 theoretical study.
;
_journal_name_full               'The Journal of organic chemistry'
_journal_paper_doi               10.1021/acs.joc.0c00767
_journal_year                    2020
_chemical_formula_moiety         '4(C8 H10 O3), H2 O'
_chemical_formula_sum            'C32 H42 O13'
_chemical_formula_weight         634.65
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   mixed
_audit_creation_date             2020-02-07
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3510 for OlexSys, GUI svn.r5506)
;
_cell_angle_alpha                99.977(2)
_cell_angle_beta                 101.184(2)
_cell_angle_gamma                90.391(2)
_cell_formula_units_Z            2
_cell_length_a                   9.7851(2)
_cell_length_b                   10.0054(3)
_cell_length_c                   17.1038(4)
_cell_measurement_reflns_used    12756
_cell_measurement_temperature    295
_cell_measurement_theta_max      70.9080
_cell_measurement_theta_min      4.5740
_cell_volume                     1616.47(7)
_computing_cell_refinement       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_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 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      295
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.3048
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.986
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
--------------------------------------------------------------------------
  1  ω     -9.00  16.00   1.00    1.00    --   34.00 102.00 -80.78   25
  2  ω     -1.00  24.00   1.00    1.00    --   38.00  95.00 173.18   25
  3  ω    -67.00  13.00   1.00    1.00    --  -41.07  57.00 120.00   80
  4  ω   -111.00 -13.00   1.00    1.00    --  -41.07 -57.00  60.00   98
  5  ω    -60.00 -17.00   1.00    1.00    --  -41.07 -38.00 150.00   43
  6  ω   -113.00 -65.00   1.00    1.00    --  -41.07 -38.00 150.00   48
  7  ω   -109.00 -17.00   1.00    1.00    --  -41.07 -57.00 -60.00   92
  8  ω     23.00  96.00   1.00    1.00    --   41.07-125.00 -30.00   73
  9  ω      6.00  31.00   1.00    1.00    --   42.00  88.00  79.64   25
 10  ω     12.00  37.00   1.00    1.00    --   46.00  83.00 -67.72   25
 11  ω     18.00  44.00   1.00    1.00    --   50.00  82.00-173.54   26
 12  ω     17.00  42.00   1.00    1.00    --   50.00  78.00  96.19   25
 13  ω     16.00  41.00   1.00    1.00    --   50.00  81.00 -16.39   25
 14  ω     22.00  48.00   1.00    1.00    --   54.00  74.00-102.70   26
 15  ω     29.00  55.00   1.00    1.00    --   62.00  77.00 121.89   26
 16  ω     34.00  60.00   1.00    1.00    --   66.00  75.00 -57.04   26
 17  ω    102.00 128.00   1.00    1.00    --   66.00  77.00  70.50   26
 18  ω     33.00  59.00   1.00    1.00    --   66.00  77.00   5.75   26
 19  ω    108.00 142.00   1.00    1.00    --   66.00  77.00   5.75   34
 20  ω    111.00 140.00   1.00    1.00    --   66.00  77.00-179.32   29
 21  ω     34.00  60.00   1.00    1.00    --   66.00  77.00  31.03   26
 22  ω     35.00  63.00   1.00    1.00    --   66.00  77.00-179.32   28
 23  ω     34.00  62.00   1.00    1.00    --   66.00  77.00  70.50   28
 24  ω     99.00 146.00   1.00    1.00    --   70.00  76.00 -44.36   47
 25  ω     38.00  75.00   1.00    1.00    --   70.00  76.00 -44.36   37
 26  ω     38.00  77.00   1.00    1.00    --   70.00  76.00-108.13   39
 27  ω     38.00  75.00   1.00    1.00    --   70.00  76.00 135.21   37
 28  ω     83.00 137.00   1.00    1.00    --   70.00  76.00 135.21   54
 29  ω     41.00  67.00   1.00    1.00    --   70.00  76.00  45.36   26
 30  ω     41.00  71.00   1.00    5.00    --   74.00  77.00-152.51   30
 31  ω     91.00 116.00   1.00    5.00    --  101.41-125.00  90.00   25
 32  ω    103.00 145.00   1.00    5.00    --  101.41  77.00 -60.00   42
 33  ω     41.00 105.00   1.00    5.00    --  101.41-125.00-150.00   64
 34  ω     69.00  95.00   1.00    5.00    --  101.41  77.00 -60.00   26
 35  ω     98.00 159.00   1.00    5.00    --  101.41  77.00  90.00   61
 36  ω     71.00  97.00   1.00    5.00    --  101.41  77.00  90.00   26
 37  ω     70.00 149.00   1.00    5.00    --  101.41  77.00  30.00   79
 38  ω     69.00 154.00   1.00    5.00    --  101.41  77.00 120.00   85
 39  ω     69.00  95.00   1.00    5.00    --  101.41  77.00 -90.00   26
 40  ω     69.00 163.00   1.00    5.00    --  101.41  77.00-120.00   94
 41  ω     84.00 114.00   1.00    5.00    --  101.41-125.00 -30.00   30
 42  ω    100.00 149.00   1.00    5.00    --  101.41  77.00  60.00   49
 43  ω     69.00  95.00   1.00    5.00    --  101.41  77.00  60.00   26
 44  ω     98.00 178.00   1.00    5.00    --  101.41  77.00 -90.00   80
 45  ω    118.00 152.00   1.00    5.00    --  101.41  77.00 150.00   34
 46  ω     69.00 113.00   1.00    5.00    --  101.41  77.00 150.00   44
 47  ω     69.00 177.00   1.00    5.00    --  101.41  77.00   0.00  108
 48  ω     32.00 130.00   1.00    5.00    --  101.41 -61.00-120.00   98
 49  ω    100.00 173.00   1.00    5.00    --  101.41  77.00 -30.00   73
 50  ω     69.00  95.00   1.00    5.00    --  101.41  77.00 -30.00   26
 51  ω     44.00 132.00   1.00    5.00    --  101.41 -77.00   0.00   88
 52  ω     65.00  96.00   1.00    5.00    --  101.41-109.00-128.00   31
 53  ω     72.00 174.00   1.00    5.00    --  101.41  77.00-180.00  102
 54  ω     69.00 165.00   1.00    5.00    --  101.41  77.00-150.00   96
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, AtlasS2'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0531073000
_diffrn_orient_matrix_UB_12      -0.1361510000
_diffrn_orient_matrix_UB_13      0.0159032000
_diffrn_orient_matrix_UB_21      -0.0738944000
_diffrn_orient_matrix_UB_22      -0.0372933000
_diffrn_orient_matrix_UB_23      -0.0894771000
_diffrn_orient_matrix_UB_31      0.1323656000
_diffrn_orient_matrix_UB_32      -0.0674999000
_diffrn_orient_matrix_UB_33      -0.0211349000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0342
_diffrn_reflns_av_unetI/netI     0.0219
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.986
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            26293
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.986
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         71.025
_diffrn_reflns_theta_min         4.491
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.848
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.77752
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.46 (Rigaku Oxford Diffraction, 2018)
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    1.304
_exptl_crystal_description       needle
_exptl_crystal_F_000             676
_exptl_crystal_size_max          0.38
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.237
_refine_diff_density_min         -0.165
_refine_diff_density_rms         0.042
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.050
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     425
_refine_ls_number_reflns         6134
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.050
_refine_ls_R_factor_all          0.0550
_refine_ls_R_factor_gt           0.0492
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0921P)²+0.2391P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1466
_refine_ls_wR_factor_ref         0.1554
_reflns_Friedel_coverage         0.000
_reflns_number_gt                5239
_reflns_number_total             6134
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            jo0c00767_si_001.cif
_cod_data_source_block           bca180
_cod_database_code               4038411
_shelx_shelxl_version_number     2016/4
_chemical_oxdiff_formula         'c10 h12 o4'
_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   0.959
_shelx_estimated_absorpt_t_min   0.739
_reflns_odcompleteness_completeness 99.96
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     64.99
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups, All O(H,H) groups
2.a Free rotating group:
 O13(H13A,H13B)
2.b Idealised Me refined as rotating group:
 C6(H6A,H6B,H6C), C7(H7A,H7B,H7C), C8(H8A,H8B,H8C), C14(H14A,H14B,H14C),
 C15(H15A,H15B,H15C), C16(H16A,H16B,H16C), C22(H22A,H22B,H22C), C23(H23A,H23B,
 H23C), C24(H24A,H24B,H24C), C30(H30A,H30B,H30C), C31(H31A,H31B,H31C), C32(H32A,
 H32B,H32C)
2.c Idealised tetrahedral OH refined as rotating group:
 O3(H3), O6(H6), O9(H9), O12(H12)
;
_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 1.436
_oxdiff_exptl_absorpt_empirical_full_min 0.711
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -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
O1 O 1.04253(12) 0.37148(12) 0.59591(7) 0.0589(3) Uani 1 1 d . . . . .
O2 O 1.23428(14) 0.26068(16) 0.60431(9) 0.0784(4) Uani 1 1 d . . . . .
O3 O 0.93724(14) 0.25370(16) 0.79160(8) 0.0737(4) Uani 1 1 d . . . . .
H3 H 0.993977 0.204852 0.813379 0.110 Uiso 1 1 calc GR . . . .
C1 C 1.13258(17) 0.28868(17) 0.63481(10) 0.0561(4) Uani 1 1 d . . . . .
C2 C 1.09991(16) 0.24510(16) 0.70400(10) 0.0536(4) Uani 1 1 d . . . . .
C3 C 0.98012(17) 0.28741(17) 0.72790(10) 0.0528(4) Uani 1 1 d . . . . .
C4 C 0.88723(16) 0.37427(17) 0.68570(10) 0.0528(4) Uani 1 1 d . . . . .
C5 C 0.92293(16) 0.41353(17) 0.62117(10) 0.0544(4) Uani 1 1 d . . . . .
C6 C 1.1992(2) 0.1550(2) 0.74631(13) 0.0741(5) Uani 1 1 d . . . . .
H6A H 1.234367 0.091386 0.706898 0.111 Uiso 1 1 calc GR . . . .
H6B H 1.151533 0.106499 0.777532 0.111 Uiso 1 1 calc GR . . . .
H6C H 1.275404 0.209303 0.781592 0.111 Uiso 1 1 calc GR . . . .
C7 C 0.75733(19) 0.4175(2) 0.71532(13) 0.0721(5) Uani 1 1 d . . . . .
H7A H 0.701304 0.338681 0.715828 0.108 Uiso 1 1 calc GR . . . .
H7B H 0.705564 0.472270 0.679971 0.108 Uiso 1 1 calc GR . . . .
H7C H 0.781829 0.469431 0.769141 0.108 Uiso 1 1 calc GR . . . .
C8 C 0.8486(2) 0.5049(2) 0.56839(13) 0.0748(5) Uani 1 1 d . . . . .
H8A H 0.908846 0.581832 0.569821 0.112 Uiso 1 1 calc GR . . . .
H8B H 0.766282 0.535455 0.587562 0.112 Uiso 1 1 calc GR . . . .
H8C H 0.822958 0.456332 0.513793 0.112 Uiso 1 1 calc GR . . . .
O4 O 0.78801(12) 0.08480(12) 0.50453(7) 0.0572(3) Uani 1 1 d . . . . .
O5 O 0.69832(16) 0.21950(16) 0.42112(9) 0.0872(5) Uani 1 1 d . . . . .
O6 O 0.47793(14) 0.13760(15) 0.63161(8) 0.0708(4) Uani 1 1 d . . . . .
H6 H 0.415394 0.183785 0.612612 0.106 Uiso 1 1 calc GR . . . .
C9 C 0.68570(18) 0.16931(17) 0.48005(10) 0.0562(4) Uani 1 1 d . . . . .
C10 C 0.57548(16) 0.19347(15) 0.52301(9) 0.0503(3) Uani 1 1 d . . . . .
C11 C 0.57595(16) 0.12704(16) 0.58670(9) 0.0502(3) Uani 1 1 d . . . . .
C12 C 0.68569(17) 0.04060(16) 0.61176(9) 0.0521(4) Uani 1 1 d . . . . .
C13 C 0.78824(17) 0.02212(16) 0.56969(9) 0.0516(3) Uani 1 1 d . . . . .
C14 C 0.46821(19) 0.29034(19) 0.49669(12) 0.0649(4) Uani 1 1 d . . . . .
H14A H 0.480315 0.372836 0.535933 0.097 Uiso 1 1 calc GR . . . .
H14B H 0.376870 0.250413 0.492091 0.097 Uiso 1 1 calc GR . . . .
H14C H 0.478423 0.310119 0.445121 0.097 Uiso 1 1 calc GR . . . .
C15 C 0.6815(2) -0.0262(2) 0.68370(12) 0.0767(6) Uani 1 1 d . . . . .
H15A H 0.697715 0.041400 0.732111 0.115 Uiso 1 1 calc GR . . . .
H15B H 0.752470 -0.091860 0.687741 0.115 Uiso 1 1 calc GR . . . .
H15C H 0.591768 -0.070711 0.677138 0.115 Uiso 1 1 calc GR . . . .
C16 C 0.91123(19) -0.0637(2) 0.58267(12) 0.0671(5) Uani 1 1 d . . . . .
H16A H 0.896918 -0.144761 0.542233 0.101 Uiso 1 1 calc GR . . . .
H16B H 0.922972 -0.087786 0.635454 0.101 Uiso 1 1 calc GR . . . .
H16C H 0.993169 -0.014111 0.578690 0.101 Uiso 1 1 calc GR . . . .
O7 O 0.76540(12) 0.48433(12) 0.13575(6) 0.0606(3) Uani 1 1 d . . . . .
O8 O 0.57054(14) 0.55708(15) 0.17036(8) 0.0773(4) Uani 1 1 d . . . . .
O9 O 0.85239(12) 0.26278(13) 0.31499(7) 0.0630(3) Uani 1 1 d . . . . .
H9 H 0.793907 0.267448 0.343710 0.095 Uiso 1 1 calc GR . . . .
C17 C 0.67284(17) 0.48866(17) 0.18618(10) 0.0556(4) Uani 1 1 d . . . . .
C18 C 0.70026(16) 0.41566(16) 0.25132(9) 0.0504(3) Uani 1 1 d . . . . .
C19 C 0.81524(15) 0.33839(15) 0.25773(9) 0.0476(3) Uani 1 1 d . . . . .
C20 C 0.90841(17) 0.33245(17) 0.20170(9) 0.0538(4) Uani 1 1 d . . . . .
C21 C 0.88070(18) 0.40796(18) 0.14359(9) 0.0568(4) Uani 1 1 d . . . . .
C22 C 0.5999(2) 0.4287(2) 0.30763(12) 0.0695(5) Uani 1 1 d . . . . .
H22A H 0.541071 0.503267 0.298703 0.104 Uiso 1 1 calc GR . . . .
H22B H 0.650533 0.444956 0.362606 0.104 Uiso 1 1 calc GR . . . .
H22C H 0.543476 0.346345 0.297736 0.104 Uiso 1 1 calc GR . . . .
C23 C 1.0310(2) 0.2447(2) 0.21089(14) 0.0786(6) Uani 1 1 d . . . . .
H23A H 1.087209 0.270804 0.264160 0.118 Uiso 1 1 calc GR . . . .
H23B H 1.085528 0.255364 0.171186 0.118 Uiso 1 1 calc GR . . . .
H23C H 0.999340 0.151472 0.203253 0.118 Uiso 1 1 calc GR . . . .
C24 C 0.9631(2) 0.4238(3) 0.08065(12) 0.0816(6) Uani 1 1 d . . . . .
H24A H 0.902867 0.449914 0.034893 0.122 Uiso 1 1 calc GR . . . .
H24B H 1.003577 0.339211 0.063772 0.122 Uiso 1 1 calc GR . . . .
H24C H 1.035787 0.492620 0.102797 0.122 Uiso 1 1 calc GR . . . .
O10 O 0.67473(12) 0.08531(12) 0.07536(7) 0.0614(3) Uani 1 1 d . . . . .
O11 O 0.82482(16) 0.08237(17) -0.00387(10) 0.0891(5) Uani 1 1 d . . . . .
O12 O 0.42095(14) 0.33992(16) -0.03722(8) 0.0755(4) Uani 1 1 d . . . . .
H12 H 0.447741 0.362628 -0.075741 0.113 Uiso 1 1 calc GR . . . .
C25 C 0.71488(18) 0.12929(18) 0.01111(11) 0.0598(4) Uani 1 1 d . . . . .
C26 C 0.63047(17) 0.21937(17) -0.02973(9) 0.0541(4) Uani 1 1 d . . . . .
C27 C 0.51125(17) 0.25771(16) -0.00394(9) 0.0527(4) Uani 1 1 d . . . . .
C28 C 0.47164(17) 0.21027(18) 0.06378(10) 0.0561(4) Uani 1 1 d . . . . .
C29 C 0.55562(18) 0.12634(17) 0.10047(10) 0.0562(4) Uani 1 1 d . . . . .
C30 C 0.6754(2) 0.2687(2) -0.09942(12) 0.0733(5) Uani 1 1 d . . . . .
H30A H 0.692769 0.365321 -0.086290 0.110 Uiso 1 1 calc GR . . . .
H30B H 0.603036 0.246834 -0.146887 0.110 Uiso 1 1 calc GR . . . .
H30C H 0.759053 0.225437 -0.109573 0.110 Uiso 1 1 calc GR . . . .
C31 C 0.3392(2) 0.2579(3) 0.08997(14) 0.0833(6) Uani 1 1 d . . . . .
H31A H 0.347970 0.354093 0.109635 0.125 Uiso 1 1 calc GR . . . .
H31B H 0.322773 0.211926 0.132294 0.125 Uiso 1 1 calc GR . . . .
H31C H 0.262544 0.238195 0.044688 0.125 Uiso 1 1 calc GR . . . .
C32 C 0.5390(2) 0.0657(2) 0.17209(12) 0.0774(6) Uani 1 1 d . . . . .
H32A H 0.557041 -0.029290 0.162215 0.116 Uiso 1 1 calc GR . . . .
H32B H 0.445608 0.077036 0.181033 0.116 Uiso 1 1 calc GR . . . .
H32C H 0.603781 0.110456 0.219078 0.116 Uiso 1 1 calc GR . . . .
O13 O 1.03080(19) 0.1067(2) 0.90421(12) 0.1012(6) Uani 1 1 d . . . . .
H13A H 1.092744 0.057523 0.925576 0.152 Uiso 1 1 d G . . . .
H13B H 0.960103 0.092793 0.924318 0.152 Uiso 1 1 d G . . . .
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'
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
C5 O1 C1 122.60(13) . . ?
C3 O3 H3 109.5 . . ?
O1 C1 C2 118.44(14) . . ?
O2 C1 O1 114.21(15) . . ?
O2 C1 C2 127.36(16) . . ?
C1 C2 C6 118.06(15) . . ?
C3 C2 C1 118.08(15) . . ?
C3 C2 C6 123.86(16) . . ?
O3 C3 C2 124.10(15) . . ?
O3 C3 C4 113.63(14) . . ?
C2 C3 C4 122.27(15) . . ?
C3 C4 C7 119.60(15) . . ?
C5 C4 C3 117.50(14) . . ?
C5 C4 C7 122.90(15) . . ?
O1 C5 C8 110.32(15) . . ?
C4 C5 O1 121.12(14) . . ?
C4 C5 C8 128.56(16) . . ?
C2 C6 H6A 109.5 . . ?
C2 C6 H6B 109.5 . . ?
C2 C6 H6C 109.5 . . ?
H6A C6 H6B 109.5 . . ?
H6A C6 H6C 109.5 . . ?
H6B C6 H6C 109.5 . . ?
C4 C7 H7A 109.5 . . ?
C4 C7 H7B 109.5 . . ?
C4 C7 H7C 109.5 . . ?
H7A C7 H7B 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
C5 C8 H8A 109.5 . . ?
C5 C8 H8B 109.5 . . ?
C5 C8 H8C 109.5 . . ?
H8A C8 H8B 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
C9 O4 C13 122.16(12) . . ?
C11 O6 H6 109.5 . . ?
O4 C9 C10 119.36(13) . . ?
O5 C9 O4 115.60(14) . . ?
O5 C9 C10 125.04(15) . . ?
C9 C10 C14 118.07(14) . . ?
C11 C10 C9 117.46(14) . . ?
C11 C10 C14 124.46(14) . . ?
O6 C11 C10 124.23(14) . . ?
O6 C11 C12 113.83(13) . . ?
C10 C11 C12 121.93(13) . . ?
C11 C12 C15 119.10(14) . . ?
C13 C12 C11 118.29(13) . . ?
C13 C12 C15 122.61(15) . . ?
O4 C13 C16 110.81(13) . . ?
C12 C13 O4 120.75(14) . . ?
C12 C13 C16 128.44(15) . . ?
C10 C14 H14A 109.5 . . ?
C10 C14 H14B 109.5 . . ?
C10 C14 H14C 109.5 . . ?
H14A C14 H14B 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C12 C15 H15A 109.5 . . ?
C12 C15 H15B 109.5 . . ?
C12 C15 H15C 109.5 . . ?
H15A C15 H15B 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C13 C16 H16A 109.5 . . ?
C13 C16 H16B 109.5 . . ?
C13 C16 H16C 109.5 . . ?
H16A C16 H16B 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C17 O7 C21 122.39(11) . . ?
C19 O9 H9 109.5 . . ?
O7 C17 C18 118.85(14) . . ?
O8 C17 O7 115.72(13) . . ?
O8 C17 C18 125.43(16) . . ?
C17 C18 C22 117.12(14) . . ?
C19 C18 C17 117.96(14) . . ?
C19 C18 C22 124.91(13) . . ?
O9 C19 C18 124.43(14) . . ?
O9 C19 C20 113.87(13) . . ?
C18 C19 C20 121.70(13) . . ?
C19 C20 C23 119.35(14) . . ?
C21 C20 C19 117.72(15) . . ?
C21 C20 C23 122.93(15) . . ?
O7 C21 C24 110.54(14) . . ?
C20 C21 O7 121.28(14) . . ?
C20 C21 C24 128.18(17) . . ?
C18 C22 H22A 109.5 . . ?
C18 C22 H22B 109.5 . . ?
C18 C22 H22C 109.5 . . ?
H22A C22 H22B 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
C20 C23 H23A 109.5 . . ?
C20 C23 H23B 109.5 . . ?
C20 C23 H23C 109.5 . . ?
H23A C23 H23B 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?
C21 C24 H24A 109.5 . . ?
C21 C24 H24B 109.5 . . ?
C21 C24 H24C 109.5 . . ?
H24A C24 H24B 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 109.5 . . ?
C29 O10 C25 121.71(12) . . ?
C27 O12 H12 109.5 . . ?
O10 C25 C26 119.09(15) . . ?
O11 C25 O10 113.51(15) . . ?
O11 C25 C26 127.41(16) . . ?
C25 C26 C30 119.03(15) . . ?
C27 C26 C25 118.03(14) . . ?
C27 C26 C30 122.94(14) . . ?
O12 C27 C26 124.67(14) . . ?
O12 C27 C28 113.55(14) . . ?
C26 C27 C28 121.78(14) . . ?
C27 C28 C31 119.16(15) . . ?
C29 C28 C27 117.67(15) . . ?
C29 C28 C31 123.17(16) . . ?
O10 C29 C32 110.47(15) . . ?
C28 C29 O10 121.73(14) . . ?
C28 C29 C32 127.79(17) . . ?
C26 C30 H30A 109.5 . . ?
C26 C30 H30B 109.5 . . ?
C26 C30 H30C 109.5 . . ?
H30A C30 H30B 109.5 . . ?
H30A C30 H30C 109.5 . . ?
H30B C30 H30C 109.5 . . ?
C28 C31 H31A 109.5 . . ?
C28 C31 H31B 109.5 . . ?
C28 C31 H31C 109.5 . . ?
H31A C31 H31B 109.5 . . ?
H31A C31 H31C 109.5 . . ?
H31B C31 H31C 109.5 . . ?
C29 C32 H32A 109.5 . . ?
C29 C32 H32B 109.5 . . ?
C29 C32 H32C 109.5 . . ?
H32A C32 H32B 109.5 . . ?
H32A C32 H32C 109.5 . . ?
H32B C32 H32C 109.5 . . ?
H13A O13 H13B 104.4 . . ?
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
O1 C1 1.371(2) . ?
O1 C5 1.369(2) . ?
O2 C1 1.223(2) . ?
O3 H3 0.8200 . ?
O3 C3 1.334(2) . ?
C1 C2 1.420(2) . ?
C2 C3 1.361(2) . ?
C2 C6 1.499(2) . ?
C3 C4 1.441(2) . ?
C4 C5 1.339(2) . ?
C4 C7 1.497(2) . ?
C5 C8 1.490(2) . ?
C6 H6A 0.9600 . ?
C6 H6B 0.9600 . ?
C6 H6C 0.9600 . ?
C7 H7A 0.9600 . ?
C7 H7B 0.9600 . ?
C7 H7C 0.9600 . ?
C8 H8A 0.9600 . ?
C8 H8B 0.9600 . ?
C8 H8C 0.9600 . ?
O4 C9 1.3654(19) . ?
O4 C13 1.3699(18) . ?
O5 C9 1.2274(19) . ?
O6 H6 0.8200 . ?
O6 C11 1.3343(18) . ?
C9 C10 1.418(2) . ?
C10 C11 1.370(2) . ?
C10 C14 1.492(2) . ?
C11 C12 1.431(2) . ?
C12 C13 1.340(2) . ?
C12 C15 1.505(2) . ?
C13 C16 1.487(2) . ?
C14 H14A 0.9600 . ?
C14 H14B 0.9600 . ?
C14 H14C 0.9600 . ?
C15 H15A 0.9600 . ?
C15 H15B 0.9600 . ?
C15 H15C 0.9600 . ?
C16 H16A 0.9600 . ?
C16 H16B 0.9600 . ?
C16 H16C 0.9600 . ?
O7 C17 1.363(2) . ?
O7 C21 1.365(2) . ?
O8 C17 1.230(2) . ?
O9 H9 0.8200 . ?
O9 C19 1.3364(17) . ?
C17 C18 1.420(2) . ?
C18 C19 1.367(2) . ?
C18 C22 1.495(2) . ?
C19 C20 1.440(2) . ?
C20 C21 1.338(2) . ?
C20 C23 1.491(2) . ?
C21 C24 1.493(2) . ?
C22 H22A 0.9600 . ?
C22 H22B 0.9600 . ?
C22 H22C 0.9600 . ?
C23 H23A 0.9600 . ?
C23 H23B 0.9600 . ?
C23 H23C 0.9600 . ?
C24 H24A 0.9600 . ?
C24 H24B 0.9600 . ?
C24 H24C 0.9600 . ?
O10 C25 1.374(2) . ?
O10 C29 1.360(2) . ?
O11 C25 1.231(2) . ?
O12 H12 0.8200 . ?
O12 C27 1.3261(19) . ?
C25 C26 1.410(2) . ?
C26 C27 1.360(2) . ?
C26 C30 1.504(2) . ?
C27 C28 1.442(2) . ?
C28 C29 1.329(2) . ?
C28 C31 1.505(3) . ?
C29 C32 1.493(2) . ?
C30 H30A 0.9600 . ?
C30 H30B 0.9600 . ?
C30 H30C 0.9600 . ?
C31 H31A 0.9600 . ?
C31 H31B 0.9600 . ?
C31 H31C 0.9600 . ?
C32 H32A 0.9600 . ?
C32 H32B 0.9600 . ?
C32 H32C 0.9600 . ?
O13 H13A 0.8504 . ?
O13 H13B 0.8506 . ?
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
O1 C1 C2 C3 0.3(2) . . . . ?
O1 C1 C2 C6 -179.79(15) . . . . ?
O2 C1 C2 C3 -179.55(18) . . . . ?
O2 C1 C2 C6 0.3(3) . . . . ?
O3 C3 C4 C5 179.66(16) . . . . ?
O3 C3 C4 C7 0.1(2) . . . . ?
C1 O1 C5 C4 -0.5(3) . . . . ?
C1 O1 C5 C8 178.60(16) . . . . ?
C1 C2 C3 O3 179.87(16) . . . . ?
C1 C2 C3 C4 -0.2(3) . . . . ?
C2 C3 C4 C5 -0.3(3) . . . . ?
C2 C3 C4 C7 -179.79(17) . . . . ?
C3 C4 C5 O1 0.6(3) . . . . ?
C3 C4 C5 C8 -178.33(18) . . . . ?
C5 O1 C1 O2 179.92(15) . . . . ?
C5 O1 C1 C2 0.0(2) . . . . ?
C6 C2 C3 O3 0.0(3) . . . . ?
C6 C2 C3 C4 179.92(17) . . . . ?
C7 C4 C5 O1 -179.87(16) . . . . ?
C7 C4 C5 C8 1.2(3) . . . . ?
O4 C9 C10 C11 -1.5(2) . . . . ?
O4 C9 C10 C14 177.74(15) . . . . ?
O5 C9 C10 C11 178.82(19) . . . . ?
O5 C9 C10 C14 -1.9(3) . . . . ?
O6 C11 C12 C13 179.15(16) . . . . ?
O6 C11 C12 C15 -0.6(2) . . . . ?
C9 O4 C13 C12 0.8(3) . . . . ?
C9 O4 C13 C16 179.98(15) . . . . ?
C9 C10 C11 O6 -178.64(16) . . . . ?
C9 C10 C11 C12 2.5(3) . . . . ?
C10 C11 C12 C13 -1.9(3) . . . . ?
C10 C11 C12 C15 178.33(17) . . . . ?
C11 C12 C13 O4 0.2(3) . . . . ?
C11 C12 C13 C16 -178.86(17) . . . . ?
C13 O4 C9 O5 179.59(17) . . . . ?
C13 O4 C9 C10 -0.1(2) . . . . ?
C14 C10 C11 O6 2.2(3) . . . . ?
C14 C10 C11 C12 -176.69(16) . . . . ?
C15 C12 C13 O4 179.96(17) . . . . ?
C15 C12 C13 C16 0.9(3) . . . . ?
O7 C17 C18 C19 -3.4(2) . . . . ?
O7 C17 C18 C22 177.01(15) . . . . ?
O8 C17 C18 C19 176.45(17) . . . . ?
O8 C17 C18 C22 -3.2(3) . . . . ?
O9 C19 C20 C21 -178.37(15) . . . . ?
O9 C19 C20 C23 1.1(2) . . . . ?
C17 O7 C21 C20 0.2(3) . . . . ?
C17 O7 C21 C24 -179.56(16) . . . . ?
C17 C18 C19 O9 -178.82(16) . . . . ?
C17 C18 C19 C20 1.3(2) . . . . ?
C18 C19 C20 C21 1.5(2) . . . . ?
C18 C19 C20 C23 -179.06(17) . . . . ?
C19 C20 C21 O7 -2.3(3) . . . . ?
C19 C20 C21 C24 177.45(18) . . . . ?
C21 O7 C17 O8 -177.13(16) . . . . ?
C21 O7 C17 C18 2.7(2) . . . . ?
C22 C18 C19 O9 0.8(3) . . . . ?
C22 C18 C19 C20 -179.08(17) . . . . ?
C23 C20 C21 O7 178.27(17) . . . . ?
C23 C20 C21 C24 -2.0(3) . . . . ?
O10 C25 C26 C27 -0.7(3) . . . . ?
O10 C25 C26 C30 179.29(17) . . . . ?
O11 C25 C26 C27 179.1(2) . . . . ?
O11 C25 C26 C30 -0.8(3) . . . . ?
O12 C27 C28 C29 179.45(16) . . . . ?
O12 C27 C28 C31 -1.0(3) . . . . ?
C25 O10 C29 C28 0.5(3) . . . . ?
C25 O10 C29 C32 -178.82(16) . . . . ?
C25 C26 C27 O12 -178.91(17) . . . . ?
C25 C26 C27 C28 0.9(3) . . . . ?
C26 C27 C28 C29 -0.4(3) . . . . ?
C26 C27 C28 C31 179.23(18) . . . . ?
C27 C28 C29 O10 -0.3(3) . . . . ?
C27 C28 C29 C32 178.83(18) . . . . ?
C29 O10 C25 O11 -179.81(16) . . . . ?
C29 O10 C25 C26 0.1(3) . . . . ?
C30 C26 C27 O12 1.1(3) . . . . ?
C30 C26 C27 C28 -179.15(17) . . . . ?
C31 C28 C29 O10 -179.90(18) . . . . ?
C31 C28 C29 C32 -0.7(3) . . . . ?
