#------------------------------------------------------------------------------
#$Date: 2023-04-07 04:28:30 +0300 (Fri, 07 Apr 2023) $
#$Revision: 282496 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/24/65/7246575.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_7246575
loop_
_publ_author_name
'Lu, Zhongyu'
'Chen, Hankun'
'Mo, Jiaxin'
'Yuan, Xiaohong'
'Wang, Dawei'
'Zheng, Xianhui'
'Zhu, Wei'
_publ_section_title
;
 Cocrystal of phloretin with isoniazid: preparation, characterization, and
 evaluation
;
_journal_issue                   16
_journal_name_full               'RSC Advances'
_journal_page_first              10914
_journal_page_last               10922
_journal_paper_doi               10.1039/D3RA00750B
_journal_volume                  13
_journal_year                    2023
_chemical_formula_moiety         'C15 H14 O5, C6 H7 N3 O'
_chemical_formula_sum            'C21 H21 N3 O6'
_chemical_formula_weight         411.41
_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
_atom_sites_solution_primary     dual
_audit_creation_date             2022-06-27
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2023-02-02 deposited with the CCDC.	2023-03-14 downloaded from the CCDC.
;
_cell_angle_alpha                92.308(3)
_cell_angle_beta                 91.398(3)
_cell_angle_gamma                107.015(3)
_cell_formula_units_Z            4
_cell_length_a                   9.8309(4)
_cell_length_b                   9.8954(4)
_cell_length_c                   20.6193(7)
_cell_measurement_reflns_used    12093
_cell_measurement_temperature    150.00(10)
_cell_measurement_theta_max      73.9310
_cell_measurement_theta_min      4.2860
_cell_volume                     1915.13(13)
_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 (Sheldrick, 2015)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      150.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2913
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 0.968
_diffrn_measured_fraction_theta_max 0.940
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     -1.00  24.00   1.00    4.00    --   38.00  95.00-112.32   25
  2  ω   -114.00 -13.00   1.00    4.00    --  -41.14 -57.00 -60.00  101
  3  ω    -91.00  -5.00   1.00    4.00    --  -41.14 125.00  60.00   86
  4  ω   -110.00 -14.00   1.00    4.00    --  -41.14 -57.00  60.00   96
  5  ω    -73.00  32.00   1.00    4.00    --  -41.14  77.00-150.00  105
  6  ω   -114.00 -13.00   1.00    4.00    --  -41.14 -57.00-180.00  101
  7  ω     24.00  78.00   1.00    4.00    --   41.14-125.00   0.00   54
  8  ω      6.00  32.00   1.00    4.00    --   42.00  90.00  91.75   26
  9  ω     11.00  38.00   1.00    4.00    --   46.00  84.00-164.09   27
 10  ω     17.00  45.00   1.00    4.00    --   46.00  79.00 -74.55   28
 11  ω     17.00  42.00   1.00    4.00    --   50.00  80.00  -2.06   25
 12  ω     17.00  42.00   1.00    4.00    --   50.00  79.00  94.31   25
 13  ω     17.00  42.00   1.00    4.00    --   50.00  80.00  31.90   25
 14  ω     87.00 114.00   1.00    4.00    --   66.00  77.00 -29.74   27
 15  ω     34.00  61.00   1.00    4.00    --   66.00  75.00 101.73   27
 16  ω     33.00  59.00   1.00    4.00    --   66.00  77.00-128.05   26
 17  ω     33.00  61.00   1.00    4.00    --   66.00  77.00 163.08   28
 18  ω     80.00 105.00   1.00    4.00    --   66.00  77.00-128.05   25
 19  ω     36.00  63.00   1.00    4.00    --   66.00  76.00   3.02   27
 20  ω     83.00 135.00   1.00    4.00    --   66.00  75.00 101.73   52
 21  ω     34.00  62.00   1.00    4.00    --   66.00  77.00 -29.74   28
 22  ω     37.00  73.00   1.00    4.00    --   70.00  77.00 135.19   36
 23  ω     37.00  65.00   1.00    4.00    --   70.00  77.00-119.88   28
 24  ω     93.00 120.00   1.00    4.00    --   70.00  77.00  54.96   27
 25  ω     38.00  64.00   1.00    4.00    --   70.00  75.00-161.65   26
 26  ω     95.00 122.00   1.00    4.00    --   70.00  75.00-161.65   27
 27  ω     38.00  81.00   1.00    4.00    --   70.00  77.00  54.96   43
 28  ω     37.00  71.00   1.00    4.00    --   70.00  77.00  30.57   34
 29  ω     37.00  80.00   1.00    4.00    --   70.00  77.00 -77.11   43
 30  ω     65.00  94.00   1.00   16.00    --   94.00  62.00 -59.75   29
 31  ω     68.00 170.00   1.00   16.00    --   98.00  64.00 164.13  102
 32  ω     75.00 146.00   1.00   16.00    --  107.79  77.00 -60.00   71
 33  ω     75.00 146.00   1.00   16.00    --  107.79  77.00   0.00   71
 34  ω     25.00 105.00   1.00   16.00    --  107.79 -94.00  90.00   80
 35  ω    109.00 170.00   1.00   16.00    --  107.79  77.00  60.00   61
 36  ω     37.00 118.00   1.00   16.00    --  107.79-125.00 -90.00   81
 37  ω     80.00 138.00   1.00   16.00    --  107.79  61.00-150.00   58
 38  ω     75.00 103.00   1.00   16.00    --  107.79  77.00  60.00   28
 39  ω     80.00 174.00   1.00   16.00    --  107.79  61.00 -90.00   94
 40  ω     75.00 101.00   1.00   16.00    --  107.79  77.00-180.00   26
 41  ω     44.00 140.00   1.00   16.00    --  107.79 -77.00 -90.00   96
 42  ω     80.00 107.00   1.00   16.00    --  107.79  61.00-180.00   27
 43  ω     75.00 175.00   1.00   16.00    --  107.79  77.00  30.00  100
 44  ω    119.00 176.00   1.00   16.00    --  107.79  77.00  90.00   57
 45  ω     75.00 102.00   1.00   16.00    --  107.79  77.00  90.00   27
 46  ω     80.00 107.00   1.00   16.00    --  107.79  61.00  90.00   27
 47  ω     72.00 118.00   1.00   16.00    --  107.79-125.00  90.00   46
 48  ω     79.00 140.00   1.00   16.00    --  107.79  61.00 -30.00   61
 49  ω     36.00  65.00   1.00   16.00    --  107.79-125.00  90.00   29
 50  ω     75.00 177.00   1.00   16.00    --  107.79  77.00 120.00  102
 51  ω     75.00 146.00   1.00   16.00    --  107.79  77.00-150.00   71
 52  ω     75.00 154.00   1.00   16.00    --  107.79  77.00 -30.00   79
 53  ω     75.00 132.00   1.00   16.00    --  107.79  77.00-120.00   57
;
_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      0.0179380000
_diffrn_orient_matrix_UB_12      -0.1431420000
_diffrn_orient_matrix_UB_13      -0.0238338000
_diffrn_orient_matrix_UB_21      0.0075266000
_diffrn_orient_matrix_UB_22      -0.0416344000
_diffrn_orient_matrix_UB_23      0.0708952000
_diffrn_orient_matrix_UB_31      -0.1628400000
_diffrn_orient_matrix_UB_32      -0.0659524000
_diffrn_orient_matrix_UB_33      -0.0022009000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0329
_diffrn_reflns_av_unetI/netI     0.0218
_diffrn_reflns_Laue_measured_fraction_full 0.968
_diffrn_reflns_Laue_measured_fraction_max 0.940
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            30217
_diffrn_reflns_point_group_measured_fraction_full 0.968
_diffrn_reflns_point_group_measured_fraction_max 0.940
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         74.702
_diffrn_reflns_theta_min         4.295
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.887
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.70682
_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    1.427
_exptl_crystal_description       plate
_exptl_crystal_F_000             864
_exptl_crystal_size_max          0.29
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.03
_refine_diff_density_max         0.536
_refine_diff_density_min         -0.360
_refine_diff_density_rms         0.095
_refine_ls_extinction_coef       0.0013(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_goodness_of_fit_ref   1.044
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     550
_refine_ls_number_reflns         7393
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.044
_refine_ls_R_factor_all          0.0932
_refine_ls_R_factor_gt           0.0878
_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)+(0.1092P)²+6.5036P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2537
_refine_ls_wR_factor_ref         0.2574
_reflns_Friedel_coverage         0.000
_reflns_number_gt                6401
_reflns_number_total             7393
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d3ra00750b1.cif
_cod_data_source_block           a22062601a0305
_cod_original_cell_volume        1915.13(12)
_cod_database_code               7246575
_shelx_shelxl_version_number     2014/7
_chemical_oxdiff_formula         CHON
_chemical_oxdiff_usercomment     GPS/YYS
_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   0.974
_shelx_estimated_absorpt_t_min   0.783
_reflns_odcompleteness_completeness 99.58
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups, All N(H,H) groups
 At 1.5 times of:
  All O(H) groups
2.a Riding coordinates:
 N1(H1A,H1B), N4(H4A,H4B)
2.b Secondary CH2 refined with riding coordinates:
 C7(H7A,H7B), C8(H8A,H8B), C22(H22A,H22B), C23(H23A,H23B)
2.c Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3A), C5(H5A), C6(H6), C12(H12), C14(H14), C17(H17), C18(H18),
 C20(H20), C21(H21), C27(H27), C29(H29), N2(H2A), C33(H33), C34(H34), C35(H35),
 C36(H36), N5(H5B), C39(H39), C40(H40), C41(H41), C42(H42)
2.d Idealised tetrahedral OH refined as rotating group:
 O1(H1), O3(H3), O4(H4), O5(H5), O6(H6A), O8(H8), O9(H9), O10(H10)
;
_olex2_date_sample_data_collection 2022-06-26
_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 1.306
_oxdiff_exptl_absorpt_empirical_full_min 0.694
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 0.6702(3) 0.3212(3) 0.35159(11) 0.0270(6) Uani 1 1 d . . . . .
H1 H 0.5858 0.2823 0.3382 0.040 Uiso 1 1 calc GR . . . .
O2 O 0.8261(3) 0.0775(3) 0.72511(12) 0.0280(6) Uani 1 1 d . . . . .
O3 O 0.9638(3) 0.0676(3) 0.82766(12) 0.0286(6) Uani 1 1 d . . . . .
H3 H 0.8955 0.0447 0.8002 0.043 Uiso 1 1 calc GR . . . .
O4 O 1.4095(3) 0.4115(3) 0.86952(12) 0.0282(6) Uani 1 1 d . . . . .
H4 H 1.4134 0.3573 0.8993 0.042 Uiso 1 1 calc GR . . . .
O5 O 1.1368(3) 0.4427(3) 0.68287(12) 0.0293(6) Uani 1 1 d . . . . .
H5 H 1.2104 0.5104 0.6783 0.044 Uiso 1 1 calc GR . . . .
C1 C 0.6878(4) 0.2846(3) 0.41401(15) 0.0205(7) Uani 1 1 d . . . . .
C2 C 0.5751(3) 0.2096(4) 0.44955(16) 0.0224(7) Uani 1 1 d . . . . .
H2 H 0.4809 0.1830 0.4311 0.027 Uiso 1 1 calc R . . . .
C3 C 0.6000(3) 0.1737(3) 0.51202(15) 0.0207(7) Uani 1 1 d . . . . .
H3A H 0.5218 0.1219 0.5358 0.025 Uiso 1 1 calc R . . . .
C4 C 0.7363(3) 0.2111(3) 0.54100(15) 0.0179(6) Uani 1 1 d . . . . .
C5 C 0.8486(4) 0.2877(4) 0.50435(16) 0.0226(7) Uani 1 1 d . . . . .
H5A H 0.9429 0.3151 0.5227 0.027 Uiso 1 1 calc R . . . .
C6 C 0.8248(4) 0.3243(4) 0.44169(16) 0.0235(7) Uani 1 1 d . . . . .
H6 H 0.9023 0.3766 0.4177 0.028 Uiso 1 1 calc R . . . .
C7 C 0.7571(3) 0.1620(3) 0.60828(15) 0.0196(7) Uani 1 1 d . . . . .
H7A H 0.6766 0.1690 0.6348 0.024 Uiso 1 1 calc R . . . .
H7B H 0.7537 0.0610 0.6044 0.024 Uiso 1 1 calc R . . . .
C8 C 0.8949(3) 0.2444(3) 0.64371(15) 0.0197(7) Uani 1 1 d . . . . .
H8A H 0.8952 0.3440 0.6510 0.024 Uiso 1 1 calc R . . . .
H8B H 0.9754 0.2437 0.6160 0.024 Uiso 1 1 calc R . . . .
C9 C 0.9170(3) 0.1854(3) 0.70846(15) 0.0194(7) Uani 1 1 d . . . . .
C10 C 1.0435(3) 0.2498(3) 0.75009(15) 0.0192(7) Uani 1 1 d . . . . .
C11 C 1.0632(4) 0.1832(3) 0.80890(15) 0.0194(6) Uani 1 1 d . . . . .
C12 C 1.1846(4) 0.2348(4) 0.84859(16) 0.0228(7) Uani 1 1 d . . . . .
H12 H 1.1961 0.1877 0.8867 0.027 Uiso 1 1 calc R . . . .
C13 C 1.2893(4) 0.3553(4) 0.83266(16) 0.0224(7) Uani 1 1 d . . . . .
C14 C 1.2735(4) 0.4267(4) 0.77738(16) 0.0222(7) Uani 1 1 d . . . . .
H14 H 1.3451 0.5102 0.7673 0.027 Uiso 1 1 calc R . . . .
C15 C 1.1528(4) 0.3749(4) 0.73718(16) 0.0216(7) Uani 1 1 d . . . . .
O6 O 0.1523(3) 0.3401(3) 0.35721(11) 0.0276(6) Uani 1 1 d . . . . .
H6A H 0.0780 0.2834 0.3401 0.041 Uiso 1 1 calc GR . . . .
O7 O 0.3279(3) 0.0815(3) 0.72559(12) 0.0283(6) Uani 1 1 d . . . . .
O8 O 0.4675(3) 0.0711(3) 0.82758(12) 0.0297(6) Uani 1 1 d . . . . .
H8 H 0.3992 0.0479 0.8001 0.045 Uiso 1 1 calc GR . . . .
O9 O 0.9151(3) 0.4123(3) 0.86728(12) 0.0280(6) Uani 1 1 d . . . . .
H9 H 0.9193 0.3577 0.8969 0.042 Uiso 1 1 calc GR . . . .
O10 O 0.6351(3) 0.4508(3) 0.68467(12) 0.0276(6) Uani 1 1 d . . . . .
H10 H 0.7119 0.5118 0.6772 0.041 Uiso 1 1 calc GR . . . .
C16 C 0.1806(4) 0.2936(4) 0.41684(16) 0.0205(7) Uani 1 1 d . . . . .
C17 C 0.1334(4) 0.1526(4) 0.43069(16) 0.0244(7) Uani 1 1 d . . . . .
H17 H 0.0800 0.0843 0.3989 0.029 Uiso 1 1 calc R . . . .
C18 C 0.1645(4) 0.1112(4) 0.49149(16) 0.0227(7) Uani 1 1 d . . . . .
H18 H 0.1325 0.0138 0.5006 0.027 Uiso 1 1 calc R . . . .
C19 C 0.2414(3) 0.2085(3) 0.53947(15) 0.0189(6) Uani 1 1 d . . . . .
C20 C 0.2892(4) 0.3495(4) 0.52396(16) 0.0254(7) Uani 1 1 d . . . . .
H20 H 0.3425 0.4181 0.5557 0.031 Uiso 1 1 calc R . . . .
C21 C 0.2605(4) 0.3924(4) 0.46315(17) 0.0264(7) Uani 1 1 d . . . . .
H21 H 0.2956 0.4891 0.4533 0.032 Uiso 1 1 calc R . . . .
C22 C 0.2659(4) 0.1557(4) 0.60572(16) 0.0219(7) Uani 1 1 d . . . . .
H22A H 0.2798 0.0610 0.5995 0.026 Uiso 1 1 calc R . . . .
H22B H 0.1791 0.1448 0.6309 0.026 Uiso 1 1 calc R . . . .
C23 C 0.3928(3) 0.2515(3) 0.64542(15) 0.0187(6) Uani 1 1 d . . . . .
H23A H 0.4792 0.2671 0.6196 0.022 Uiso 1 1 calc R . . . .
H23B H 0.3766 0.3446 0.6543 0.022 Uiso 1 1 calc R . . . .
C24 C 0.4180(3) 0.1905(3) 0.70916(15) 0.0187(6) Uani 1 1 d . . . . .
C25 C 0.5445(3) 0.2546(3) 0.75053(15) 0.0183(6) Uani 1 1 d . . . . .
C26 C 0.5662(4) 0.1868(4) 0.80892(15) 0.0200(7) Uani 1 1 d . . . . .
C27 C 0.6888(4) 0.2373(4) 0.84775(16) 0.0227(7) Uani 1 1 d . . . . .
H27 H 0.7012 0.1901 0.8857 0.027 Uiso 1 1 calc R . . . .
C28 C 0.7937(4) 0.3573(4) 0.83105(16) 0.0219(7) Uani 1 1 d . . . . .
C29 C 0.7769(4) 0.4292(4) 0.77614(16) 0.0213(7) Uani 1 1 d . . . . .
H29 H 0.8492 0.5117 0.7654 0.026 Uiso 1 1 calc R . . . .
C30 C 0.6540(4) 0.3795(3) 0.73737(15) 0.0197(7) Uani 1 1 d . . . . .
O11 O 0.2140(2) 0.2400(3) 0.20861(12) 0.0254(5) Uani 1 1 d . . . . .
N1 N 0.4084(3) 0.1937(3) 0.29326(13) 0.0237(6) Uani 1 1 d . . . . .
H1A H 0.3647 0.1031 0.2981 0.028 Uiso 1 1 d R . . . .
H1B H 0.3642 0.2527 0.3062 0.028 Uiso 1 1 d R . . . .
N2 N 0.4264(3) 0.2025(3) 0.22551(14) 0.0236(6) Uani 1 1 d . . . . .
H2A H 0.5041 0.1916 0.2086 0.028 Uiso 1 1 calc R . . . .
N3 N 0.4076(3) 0.2820(3) -0.01487(14) 0.0286(7) Uani 1 1 d . . . . .
C31 C 0.3259(3) 0.2273(3) 0.18723(16) 0.0189(6) Uani 1 1 d . . . . .
C32 C 0.3573(3) 0.2435(3) 0.11665(16) 0.0197(7) Uani 1 1 d . . . . .
C33 C 0.4331(4) 0.1681(4) 0.08269(18) 0.0307(8) Uani 1 1 d . . . . .
H33 H 0.4702 0.1024 0.1039 0.037 Uiso 1 1 calc R . . . .
C34 C 0.4541(5) 0.1896(4) 0.01768(18) 0.0333(9) Uani 1 1 d . . . . .
H34 H 0.5045 0.1355 -0.0052 0.040 Uiso 1 1 calc R . . . .
C35 C 0.3359(5) 0.3547(5) 0.0188(2) 0.0394(10) Uani 1 1 d . . . . .
H35 H 0.3027 0.4220 -0.0033 0.047 Uiso 1 1 calc R . . . .
C36 C 0.3065(5) 0.3388(4) 0.08342(19) 0.0337(9) Uani 1 1 d . . . . .
H36 H 0.2528 0.3918 0.1047 0.040 Uiso 1 1 calc R . . . .
O12 O -0.2866(3) 0.2370(3) 0.20551(12) 0.0264(6) Uani 1 1 d . . . . .
N4 N -0.0938(3) 0.1867(3) 0.29052(13) 0.0223(6) Uani 1 1 d . . . . .
H4A H -0.1274 0.0995 0.3040 0.027 Uiso 1 1 d R . . . .
H4B H -0.1419 0.2455 0.2968 0.027 Uiso 1 1 d R . . . .
N5 N -0.0750(3) 0.1978(3) 0.22290(13) 0.0217(6) Uani 1 1 d . . . . .
H5B H 0.0029 0.1874 0.2060 0.026 Uiso 1 1 calc R . . . .
N6 N -0.0894(3) 0.2821(3) -0.01698(14) 0.0279(7) Uani 1 1 d . . . . .
C37 C -0.1750(3) 0.2240(3) 0.18455(16) 0.0186(6) Uani 1 1 d . . . . .
C38 C -0.1414(3) 0.2418(3) 0.11415(15) 0.0189(6) Uani 1 1 d . . . . .
C39 C -0.0644(4) 0.1675(4) 0.08068(18) 0.0294(8) Uani 1 1 d . . . . .
H39 H -0.0277 0.1015 0.1019 0.035 Uiso 1 1 calc R . . . .
C40 C -0.0417(4) 0.1907(4) 0.01572(18) 0.0321(9) Uani 1 1 d . . . . .
H40 H 0.0110 0.1385 -0.0070 0.039 Uiso 1 1 calc R . . . .
C41 C -0.1627(5) 0.3533(5) 0.01641(19) 0.0380(10) Uani 1 1 d . . . . .
H41 H -0.1964 0.4202 -0.0058 0.046 Uiso 1 1 calc R . . . .
C42 C -0.1932(5) 0.3365(4) 0.08112(18) 0.0329(9) Uani 1 1 d . . . . .
H42 H -0.2481 0.3885 0.1024 0.039 Uiso 1 1 calc R . . . .
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
C1 O1 H1 109.5 . . ?
C11 O3 H3 109.5 . . ?
C13 O4 H4 109.5 . . ?
C15 O5 H5 109.5 . . ?
O1 C1 C2 122.5(3) . . ?
O1 C1 C6 117.9(3) . . ?
C2 C1 C6 119.6(3) . . ?
C1 C2 H2 120.1 . . ?
C1 C2 C3 119.8(3) . . ?
C3 C2 H2 120.1 . . ?
C2 C3 H3A 119.0 . . ?
C2 C3 C4 122.0(3) . . ?
C4 C3 H3A 119.0 . . ?
C3 C4 C5 117.2(3) . . ?
C3 C4 C7 119.3(3) . . ?
C5 C4 C7 123.4(3) . . ?
C4 C5 H5A 119.4 . . ?
C6 C5 C4 121.2(3) . . ?
C6 C5 H5A 119.4 . . ?
C1 C6 C5 120.2(3) . . ?
C1 C6 H6 119.9 . . ?
C5 C6 H6 119.9 . . ?
C4 C7 H7A 108.6 . . ?
C4 C7 H7B 108.6 . . ?
H7A C7 H7B 107.6 . . ?
C8 C7 C4 114.6(3) . . ?
C8 C7 H7A 108.6 . . ?
C8 C7 H7B 108.6 . . ?
C7 C8 H8A 109.0 . . ?
C7 C8 H8B 109.0 . . ?
C7 C8 C9 113.1(3) . . ?
H8A C8 H8B 107.8 . . ?
C9 C8 H8A 109.0 . . ?
C9 C8 H8B 109.0 . . ?
O2 C9 C8 118.4(3) . . ?
O2 C9 C10 120.0(3) . . ?
C10 C9 C8 121.6(3) . . ?
C11 C10 C9 118.9(3) . . ?
C15 C10 C9 125.2(3) . . ?
C15 C10 C11 115.8(3) . . ?
O3 C11 C10 121.2(3) . . ?
O3 C11 C12 117.1(3) . . ?
C12 C11 C10 121.7(3) . . ?
C11 C12 H12 120.1 . . ?
C11 C12 C13 119.9(3) . . ?
C13 C12 H12 120.1 . . ?
O4 C13 C12 122.8(3) . . ?
O4 C13 C14 116.4(3) . . ?
C12 C13 C14 120.8(3) . . ?
C13 C14 H14 120.2 . . ?
C15 C14 C13 119.6(3) . . ?
C15 C14 H14 120.2 . . ?
O5 C15 C10 117.7(3) . . ?
O5 C15 C14 120.2(3) . . ?
C14 C15 C10 122.1(3) . . ?
C16 O6 H6A 109.5 . . ?
C26 O8 H8 109.5 . . ?
C28 O9 H9 109.5 . . ?
C30 O10 H10 109.5 . . ?
O6 C16 C21 118.3(3) . . ?
C17 C16 O6 121.8(3) . . ?
C17 C16 C21 119.9(3) . . ?
C16 C17 H17 120.2 . . ?
C16 C17 C18 119.5(3) . . ?
C18 C17 H17 120.2 . . ?
C17 C18 H18 119.1 . . ?
C17 C18 C19 121.8(3) . . ?
C19 C18 H18 119.1 . . ?
C18 C19 C22 118.7(3) . . ?
C20 C19 C18 117.5(3) . . ?
C20 C19 C22 123.8(3) . . ?
C19 C20 H20 119.3 . . ?
C21 C20 C19 121.4(3) . . ?
C21 C20 H20 119.3 . . ?
C16 C21 C20 119.8(3) . . ?
C16 C21 H21 120.1 . . ?
C20 C21 H21 120.1 . . ?
C19 C22 H22A 108.6 . . ?
C19 C22 H22B 108.6 . . ?
C19 C22 C23 114.6(3) . . ?
H22A C22 H22B 107.6 . . ?
C23 C22 H22A 108.6 . . ?
C23 C22 H22B 108.6 . . ?
C22 C23 H23A 109.1 . . ?
C22 C23 H23B 109.1 . . ?
H23A C23 H23B 107.8 . . ?
C24 C23 C22 112.7(3) . . ?
C24 C23 H23A 109.1 . . ?
C24 C23 H23B 109.1 . . ?
O7 C24 C23 118.3(3) . . ?
O7 C24 C25 119.9(3) . . ?
C25 C24 C23 121.8(3) . . ?
C26 C25 C24 119.1(3) . . ?
C30 C25 C24 125.1(3) . . ?
C30 C25 C26 115.7(3) . . ?
O8 C26 C25 121.0(3) . . ?
O8 C26 C27 117.3(3) . . ?
C27 C26 C25 121.7(3) . . ?
C26 C27 H27 120.2 . . ?
C26 C27 C28 119.7(3) . . ?
C28 C27 H27 120.2 . . ?
O9 C28 C27 122.4(3) . . ?
O9 C28 C29 116.5(3) . . ?
C27 C28 C29 121.1(3) . . ?
C28 C29 H29 120.3 . . ?
C30 C29 C28 119.4(3) . . ?
C30 C29 H29 120.3 . . ?
O10 C30 C25 117.8(3) . . ?
O10 C30 C29 119.9(3) . . ?
C29 C30 C25 122.3(3) . . ?
H1A N1 H1B 116.4 . . ?
N2 N1 H1A 104.0 . . ?
N2 N1 H1B 109.3 . . ?
N1 N2 H2A 119.9 . . ?
C31 N2 N1 120.1(3) . . ?
C31 N2 H2A 119.9 . . ?
C34 N3 C35 116.3(3) . . ?
O11 C31 N2 122.1(3) . . ?
O11 C31 C32 121.2(3) . . ?
N2 C31 C32 116.7(3) . . ?
C33 C32 C31 123.8(3) . . ?
C33 C32 C36 118.0(3) . . ?
C36 C32 C31 118.1(3) . . ?
C32 C33 H33 120.4 . . ?
C34 C33 C32 119.1(3) . . ?
C34 C33 H33 120.4 . . ?
N3 C34 C33 123.7(4) . . ?
N3 C34 H34 118.2 . . ?
C33 C34 H34 118.2 . . ?
N3 C35 H35 117.8 . . ?
N3 C35 C36 124.5(4) . . ?
C36 C35 H35 117.8 . . ?
C32 C36 H36 120.8 . . ?
C35 C36 C32 118.3(4) . . ?
C35 C36 H36 120.8 . . ?
H4A N4 H4B 119.1 . . ?
N5 N4 H4A 115.9 . . ?
N5 N4 H4B 99.7 . . ?
N4 N5 H5B 119.8 . . ?
C37 N5 N4 120.3(3) . . ?
C37 N5 H5B 119.8 . . ?
C40 N6 C41 116.4(3) . . ?
O12 C37 N5 122.4(3) . . ?
O12 C37 C38 121.4(3) . . ?
N5 C37 C38 116.2(3) . . ?
C39 C38 C37 123.7(3) . . ?
C39 C38 C42 118.5(3) . . ?
C42 C38 C37 117.8(3) . . ?
C38 C39 H39 120.6 . . ?
C38 C39 C40 118.8(3) . . ?
C40 C39 H39 120.6 . . ?
N6 C40 C39 123.8(3) . . ?
N6 C40 H40 118.1 . . ?
C39 C40 H40 118.1 . . ?
N6 C41 H41 117.8 . . ?
N6 C41 C42 124.4(3) . . ?
C42 C41 H41 117.8 . . ?
C38 C42 H42 121.0 . . ?
C41 C42 C38 118.0(3) . . ?
C41 C42 H42 121.0 . . ?
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 H1 0.8400 . ?
O1 C1 1.372(4) . ?
O2 C9 1.242(4) . ?
O3 H3 0.8400 . ?
O3 C11 1.346(4) . ?
O4 H4 0.8400 . ?
O4 C13 1.349(4) . ?
O5 H5 0.8400 . ?
O5 C15 1.358(4) . ?
C1 C2 1.385(5) . ?
C1 C6 1.388(5) . ?
C2 H2 0.9500 . ?
C2 C3 1.385(5) . ?
C3 H3A 0.9500 . ?
C3 C4 1.394(4) . ?
C4 C5 1.400(5) . ?
C4 C7 1.517(4) . ?
C5 H5A 0.9500 . ?
C5 C6 1.389(5) . ?
C6 H6 0.9500 . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C7 C8 1.514(4) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C8 C9 1.514(4) . ?
C9 C10 1.459(4) . ?
C10 C11 1.439(4) . ?
C10 C15 1.422(5) . ?
C11 C12 1.385(5) . ?
C12 H12 0.9500 . ?
C12 C13 1.385(5) . ?
C13 C14 1.394(5) . ?
C14 H14 0.9500 . ?
C14 C15 1.385(5) . ?
O6 H6A 0.8400 . ?
O6 C16 1.380(4) . ?
O7 C24 1.244(4) . ?
O8 H8 0.8400 . ?
O8 C26 1.343(4) . ?
O9 H9 0.8400 . ?
O9 C28 1.350(4) . ?
O10 H10 0.8400 . ?
O10 C30 1.357(4) . ?
C16 C17 1.380(5) . ?
C16 C21 1.387(5) . ?
C17 H17 0.9500 . ?
C17 C18 1.389(5) . ?
C18 H18 0.9500 . ?
C18 C19 1.392(5) . ?
C19 C20 1.390(5) . ?
C19 C22 1.520(4) . ?
C20 H20 0.9500 . ?
C20 C21 1.388(5) . ?
C21 H21 0.9500 . ?
C22 H22A 0.9900 . ?
C22 H22B 0.9900 . ?
C22 C23 1.524(4) . ?
C23 H23A 0.9900 . ?
C23 H23B 0.9900 . ?
C23 C24 1.513(4) . ?
C24 C25 1.456(4) . ?
C25 C26 1.443(4) . ?
C25 C30 1.422(5) . ?
C26 C27 1.383(5) . ?
C27 H27 0.9500 . ?
C27 C28 1.388(5) . ?
C28 C29 1.393(5) . ?
C29 H29 0.9500 . ?
C29 C30 1.384(5) . ?
O11 C31 1.233(4) . ?
N1 H1A 0.8849 . ?
N1 H1B 0.8619 . ?
N1 N2 1.415(4) . ?
N2 H2A 0.8800 . ?
N2 C31 1.333(4) . ?
N3 C34 1.332(5) . ?
N3 C35 1.334(5) . ?
C31 C32 1.500(4) . ?
C32 C33 1.382(5) . ?
C32 C36 1.386(5) . ?
C33 H33 0.9500 . ?
C33 C34 1.377(5) . ?
C34 H34 0.9500 . ?
C35 H35 0.9500 . ?
C35 C36 1.375(6) . ?
C36 H36 0.9500 . ?
O12 C37 1.229(4) . ?
N4 H4A 0.8872 . ?
N4 H4B 0.8592 . ?
N4 N5 1.415(4) . ?
N5 H5B 0.8800 . ?
N5 C37 1.337(4) . ?
N6 C40 1.332(5) . ?
N6 C41 1.332(5) . ?
C37 C38 1.502(4) . ?
C38 C39 1.378(5) . ?
C38 C42 1.385(5) . ?
C39 H39 0.9500 . ?
C39 C40 1.381(5) . ?
C40 H40 0.9500 . ?
C41 H41 0.9500 . ?
C41 C42 1.380(5) . ?
C42 H42 0.9500 . ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O1 H1 N1 0.84 1.91 2.736(4) 169.9 .
O1 H1 N2 0.84 2.73 3.418(4) 140.8 .
O3 H3 O2 0.84 1.76 2.504(3) 147.1 .
O4 H4 N3 0.84 1.94 2.750(4) 160.8 1_656
O5 H5 O1 0.84 1.87 2.677(3) 159.8 2_766
C6 H6 O5 0.95 2.88 3.474(4) 121.5 2_766
C12 H12 N3 0.95 2.80 3.456(5) 127.3 1_656
O6 H6A N4 0.84 1.92 2.751(4) 168.0 .
O6 H6A N5 0.84 2.78 3.492(4) 143.5 .
O8 H8 O7 0.84 1.76 2.505(3) 147.3 .
O9 H9 N6 0.84 1.95 2.753(4) 159.9 1_656
O10 H10 O6 0.84 1.85 2.664(3) 163.3 2_666
C27 H27 N6 0.95 2.77 3.431(4) 127.7 1_656
N1 H1A O2 0.88 2.21 2.986(4) 146.8 2_656
N2 H2A O8 0.88 2.77 3.330(4) 122.8 2_656
N2 H2A O12 0.88 1.98 2.784(4) 151.9 1_655
C33 H33 O8 0.95 2.47 3.406(4) 169.9 2_656
N4 H4A O7 0.89 2.29 2.961(4) 132.1 2_556
N4 H4B O1 0.86 2.47 3.250(4) 151.6 1_455
N5 H5B O3 0.88 2.70 3.270(4) 123.3 2_656
N5 H5B O11 0.88 1.99 2.773(4) 148.3 .
C39 H39 O3 0.95 2.46 3.402(4) 169.5 2_656
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 178.9(3) . . . . ?
O1 C1 C6 C5 -178.9(3) . . . . ?
O2 C9 C10 C11 2.4(5) . . . . ?
O2 C9 C10 C15 -178.3(3) . . . . ?
O3 C11 C12 C13 -178.5(3) . . . . ?
O4 C13 C14 C15 179.9(3) . . . . ?
C1 C2 C3 C4 0.3(5) . . . . ?
C2 C1 C6 C5 0.7(5) . . . . ?
C2 C3 C4 C5 0.2(5) . . . . ?
C2 C3 C4 C7 -177.0(3) . . . . ?
C3 C4 C5 C6 -0.2(5) . . . . ?
C3 C4 C7 C8 -161.2(3) . . . . ?
C4 C5 C6 C1 -0.3(5) . . . . ?
C4 C7 C8 C9 -175.6(3) . . . . ?
C5 C4 C7 C8 21.9(5) . . . . ?
C6 C1 C2 C3 -0.7(5) . . . . ?
C7 C4 C5 C6 176.8(3) . . . . ?
C7 C8 C9 O2 1.8(4) . . . . ?
C7 C8 C9 C10 180.0(3) . . . . ?
C8 C9 C10 C11 -175.7(3) . . . . ?
C8 C9 C10 C15 3.5(5) . . . . ?
C9 C10 C11 O3 -3.6(5) . . . . ?
C9 C10 C11 C12 176.4(3) . . . . ?
C9 C10 C15 O5 2.1(5) . . . . ?
C9 C10 C15 C14 -176.9(3) . . . . ?
C10 C11 C12 C13 1.4(5) . . . . ?
C11 C10 C15 O5 -178.6(3) . . . . ?
C11 C10 C15 C14 2.4(5) . . . . ?
C11 C12 C13 O4 179.5(3) . . . . ?
C11 C12 C13 C14 0.7(5) . . . . ?
C12 C13 C14 C15 -1.2(5) . . . . ?
C13 C14 C15 O5 -179.4(3) . . . . ?
C13 C14 C15 C10 -0.4(5) . . . . ?
C15 C10 C11 O3 177.1(3) . . . . ?
C15 C10 C11 C12 -2.9(5) . . . . ?
O6 C16 C17 C18 -179.9(3) . . . . ?
O6 C16 C21 C20 179.1(3) . . . . ?
O7 C24 C25 C26 2.5(5) . . . . ?
O7 C24 C25 C30 -179.4(3) . . . . ?
O8 C26 C27 C28 -179.4(3) . . . . ?
O9 C28 C29 C30 -179.1(3) . . . . ?
C16 C17 C18 C19 0.6(5) . . . . ?
C17 C16 C21 C20 -1.9(5) . . . . ?
C17 C18 C19 C20 -1.4(5) . . . . ?
C17 C18 C19 C22 177.5(3) . . . . ?
C18 C19 C20 C21 0.5(5) . . . . ?
C18 C19 C22 C23 157.7(3) . . . . ?
C19 C20 C21 C16 1.1(6) . . . . ?
C19 C22 C23 C24 -176.6(3) . . . . ?
C20 C19 C22 C23 -23.5(5) . . . . ?
C21 C16 C17 C18 1.1(5) . . . . ?
C22 C19 C20 C21 -178.3(3) . . . . ?
C22 C23 C24 O7 -7.6(4) . . . . ?
C22 C23 C24 C25 171.4(3) . . . . ?
C23 C24 C25 C26 -176.5(3) . . . . ?
C23 C24 C25 C30 1.6(5) . . . . ?
C24 C25 C26 O8 -4.2(5) . . . . ?
C24 C25 C26 C27 175.5(3) . . . . ?
C24 C25 C30 O10 4.9(5) . . . . ?
C24 C25 C30 C29 -175.0(3) . . . . ?
C25 C26 C27 C28 0.8(5) . . . . ?
C26 C25 C30 O10 -176.9(3) . . . . ?
C26 C25 C30 C29 3.2(5) . . . . ?
C26 C27 C28 O9 179.4(3) . . . . ?
C26 C27 C28 C29 0.9(5) . . . . ?
C27 C28 C29 C30 -0.5(5) . . . . ?
C28 C29 C30 O10 178.4(3) . . . . ?
C28 C29 C30 C25 -1.7(5) . . . . ?
C30 C25 C26 O8 177.5(3) . . . . ?
C30 C25 C26 C27 -2.7(5) . . . . ?
O11 C31 C32 C33 -146.4(4) . . . . ?
O11 C31 C32 C36 33.1(5) . . . . ?
N1 N2 C31 O11 -1.7(5) . . . . ?
N1 N2 C31 C32 176.5(3) . . . . ?
N2 C31 C32 C33 35.5(5) . . . . ?
N2 C31 C32 C36 -145.1(4) . . . . ?
N3 C35 C36 C32 1.6(7) . . . . ?
C31 C32 C33 C34 179.0(4) . . . . ?
C31 C32 C36 C35 179.6(4) . . . . ?
C32 C33 C34 N3 1.4(7) . . . . ?
C33 C32 C36 C35 -0.9(6) . . . . ?
C34 N3 C35 C36 -0.8(7) . . . . ?
C35 N3 C34 C33 -0.8(6) . . . . ?
C36 C32 C33 C34 -0.5(6) . . . . ?
O12 C37 C38 C39 -147.0(4) . . . . ?
O12 C37 C38 C42 31.7(5) . . . . ?
N4 N5 C37 O12 -1.2(5) . . . . ?
N4 N5 C37 C38 176.7(3) . . . . ?
N5 C37 C38 C39 35.0(5) . . . . ?
N5 C37 C38 C42 -146.2(3) . . . . ?
N6 C41 C42 C38 1.6(7) . . . . ?
C37 C38 C39 C40 179.0(4) . . . . ?
C37 C38 C42 C41 -180.0(4) . . . . ?
C38 C39 C40 N6 0.4(7) . . . . ?
C39 C38 C42 C41 -1.1(6) . . . . ?
C40 N6 C41 C42 -1.0(7) . . . . ?
C41 N6 C40 C39 0.0(6) . . . . ?
C42 C38 C39 C40 0.2(6) . . . . ?
