#------------------------------------------------------------------------------
#$Date: 2023-10-10 00:56:30 +0300 (Tue, 10 Oct 2023) $
#$Revision: 286850 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/13/21/7132186.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_7132186
loop_
_publ_author_name
'Ahsan, Mollah Rohan'
'Singh, Lavanya'
'Varma, Harshit'
'Mukherjee, Arijit'
_publ_section_title
;
 Exploiting benzilic acid as a modular template: controlling
 photoreactivity and solid to liquid transition during photodimerization.
;
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_paper_doi               10.1039/d3cc04257j
_journal_year                    2023
_chemical_formula_moiety         'C14 H11 O3, C13 H10 N'
_chemical_formula_sum            'C27 H21 N O3'
_chemical_formula_weight         407.45
_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             2023-08-11
_audit_creation_method
;
Olex2 1.5
(compiled 2023.03.06 svn.rbb2c1857 for OlexSys, GUI svn.r6748)
;
_audit_update_record
;
2023-08-21 deposited with the CCDC.	2023-09-27 downloaded from the CCDC.
;
_cell_angle_alpha                93.589(2)
_cell_angle_beta                 94.776(2)
_cell_angle_gamma                99.891(2)
_cell_formula_units_Z            4
_cell_length_a                   6.7453(2)
_cell_length_b                   16.8984(3)
_cell_length_c                   18.0463(4)
_cell_measurement_reflns_used    6754
_cell_measurement_temperature    140
_cell_measurement_theta_max      79.1540
_cell_measurement_theta_min      4.9510
_cell_volume                     2013.19(8)
_computing_cell_refinement       'CrysAlisPro 1.171.39.20a (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.39.20a (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.39.20a (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2019/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      140.00
_diffrn_detector                 'CCD plate'
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.966
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -89.00 -15.00   0.50    0.50    --    0.00 -57.00-150.00  148
  2  ω     17.00  43.00   0.50    0.50    --    0.00  37.00-180.00   52
  3  ω    -89.00 -33.00   0.50    0.50    --    0.00 -37.00 -30.00  112
  4  ω     22.00  89.00   0.50    0.50    --    0.00  37.00  90.00  134
  5  ω    -11.00  15.00   0.50    0.50    --    0.00 -57.00-150.00   52
  6  ω    -29.00  47.00   0.50    0.50    --    0.00  82.00 -90.00  152
  7  ω     56.00  87.00   0.50    0.50    --    0.00  82.00 -90.00   62
  8  ω     25.00 126.00   0.50    0.60    --  107.20 -61.00 150.00  202
  9  ω     80.00 192.00   0.50    0.60    --  107.20  15.00 -90.00  224
 10  ω     61.00  87.00   0.50    0.60    --  107.20 -45.00 -30.00   52
 11  ω     88.00 114.00   0.50    0.60    --  107.20 -82.00 -60.00   52
 12  ω     27.00  53.00   0.50    0.60    --  107.20 -82.00  90.00   52
 13  ω     77.00 140.00   0.50    0.60    --  107.20 -82.00  90.00  126
 14  ω     20.00  62.00   0.50    0.60    --  107.20 -30.00-120.00   84
 15  ω     41.00  75.00   0.50    0.60    --  107.20 -82.00 -60.00   68
 16  ω     89.00 197.00   0.50    0.60    --  107.20  30.00-150.00  216
 17  ω     33.00  98.00   0.50    0.60    --  107.20 -15.00-120.00  130
 18  ω     61.00 132.00   0.50    0.60    --  107.20 -61.00   0.00  142
 19  ω     88.00 140.00   0.50    0.60    --  107.20 -82.00-150.00  104
 20  ω     87.00 196.00   0.50    0.60    --  107.20  45.00 150.00  218
 21  ω     28.00  54.00   0.50    0.60    --  107.20 -61.00   0.00   52
 22  ω     43.00 139.00   0.50    0.60    --  107.20 -82.00   0.00  192
 23  ω     61.00 110.00   0.50    0.60    --  107.20 -30.00 120.00   98
 24  ω     86.00 114.00   0.50    0.60    --  107.20 -82.00  30.00   56
 25  ω     79.00 110.00   0.50    0.60    --  107.20 -82.00-120.00   62
 26  ω     74.00 121.00   0.50    0.60    --  107.20 -30.00-120.00   94
 27  ω     21.00 138.00   0.50    0.60    --  107.20 -82.00 150.00  234
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Pro: Kappa dual home/near'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.1006914000
_diffrn_orient_matrix_UB_12      -0.0621899000
_diffrn_orient_matrix_UB_13      -0.0640397000
_diffrn_orient_matrix_UB_21      -0.1885775000
_diffrn_orient_matrix_UB_22      -0.0195834000
_diffrn_orient_matrix_UB_23      0.0427466000
_diffrn_orient_matrix_UB_31      -0.0924370000
_diffrn_orient_matrix_UB_32      0.0660736000
_diffrn_orient_matrix_UB_33      -0.0381498000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0527
_diffrn_reflns_av_unetI/netI     0.0595
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.966
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            23775
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.966
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         79.662
_diffrn_reflns_theta_min         4.934
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.701
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.50413
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.20a (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.344
_exptl_crystal_description       block
_exptl_crystal_F_000             856
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.276
_refine_diff_density_min         -0.230
_refine_diff_density_rms         0.051
_refine_ls_extinction_coef       0.0012(2)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2019/2 (Sheldrick 2019)'
_refine_ls_goodness_of_fit_ref   1.066
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     576
_refine_ls_number_reflns         8483
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.066
_refine_ls_R_factor_all          0.0652
_refine_ls_R_factor_gt           0.0511
_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)+(0.0690P)²+0.1399P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1363
_refine_ls_wR_factor_ref         0.1477
_reflns_Friedel_coverage         0.000
_reflns_number_gt                6467
_reflns_number_total             8483
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d3cc04257j2.cif
_cod_data_source_block           exp_1357-am-l-284-etoh
_cod_database_code               7132186
_shelx_shelxl_version_number     2019/3
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_shelx_estimated_absorpt_t_max   0.933
_shelx_estimated_absorpt_t_min   0.873
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C57(H57), C39(H39), C49(H49), C62(H62), C61(H61), C52(H52), C60(H60),
 C17(H17), C59(H59), C44(H44), C48(H48), C40(H40), C31(H31), C19(H19), C33(H33),
  C37(H37), C46(H46), C16(H16), C42(H42), C13(H13), C27(H27), C53(H53),
 C55(H55), C47(H47), C41(H41), C54(H54), C29(H29), C14(H14), C30(H30), C23(H23),
  C15(H15), C20(H20), C28(H28), C34(H34), C22(H22), C21(H21), C36(H36), C35(H35)
;
_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 2.078
_oxdiff_exptl_absorpt_empirical_full_min 0.570
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
O6 O 1.01791(19) 0.55839(7) 0.35677(7) 0.0346(3) Uani 1 1 d . . . . .
O1 O 0.7602(2) -0.00046(7) 0.30587(7) 0.0369(3) Uani 1 1 d . . . . .
O4 O 0.6936(2) 0.47760(7) 0.19348(7) 0.0370(3) Uani 1 1 d . . . . .
O3 O 0.4549(2) 0.02555(9) 0.14190(8) 0.0421(3) Uani 1 1 d . . . . .
O5 O 1.0195(2) 0.48079(8) 0.23119(8) 0.0423(3) Uani 1 1 d . . . . .
N7 N 0.7604(2) 0.03004(8) 0.44712(8) 0.0255(3) Uani 1 1 d . . . . .
N8 N 0.7289(2) 0.45743(8) 0.05265(8) 0.0268(3) Uani 1 1 d . . . . .
O2 O 0.4406(2) -0.05231(8) 0.26095(8) 0.0464(4) Uani 1 1 d . . . . .
C63 C 0.7601(2) 0.52715(9) 0.01897(9) 0.0250(3) Uani 1 1 d . . . . .
C58 C 0.7573(2) 0.52593(10) -0.06030(9) 0.0267(3) Uani 1 1 d . . . . .
C26 C 0.6805(3) 0.48183(9) 0.35990(9) 0.0272(3) Uani 1 1 d . . . . .
C50 C 0.8152(2) 0.10868(9) 0.47156(9) 0.0252(3) Uani 1 1 d . . . . .
C38 C 0.7306(2) -0.02937(10) 0.49441(9) 0.0255(3) Uani 1 1 d . . . . .
C51 C 0.6938(2) 0.38445(10) 0.01352(9) 0.0265(3) Uani 1 1 d . . . . .
C57 C 0.7195(3) 0.45107(10) -0.10147(10) 0.0299(4) Uani 1 1 d . . . . .
H57 H 0.716473 0.448897 -0.154292 0.036 Uiso 1 1 calc R U . . .
C39 C 0.6704(2) -0.11060(10) 0.46485(10) 0.0299(4) Uani 1 1 d . . . . .
H39 H 0.651347 -0.123535 0.412453 0.036 Uiso 1 1 calc R U . . .
C49 C 0.8398(3) 0.16830(10) 0.41937(10) 0.0303(4) Uani 1 1 d . . . . .
H49 H 0.821333 0.153324 0.367296 0.036 Uiso 1 1 calc R U . . .
C32 C 0.7499(3) 0.61718(9) 0.30262(9) 0.0291(4) Uani 1 1 d . . . . .
C45 C 0.8476(2) 0.13118(10) 0.54969(10) 0.0286(3) Uani 1 1 d . . . . .
C56 C 0.6864(2) 0.37978(10) -0.06617(10) 0.0287(3) Uani 1 1 d . . . . .
C25 C 0.8225(3) 0.53813(9) 0.31658(9) 0.0271(3) Uani 1 1 d . . . . .
C24 C 0.8488(3) 0.49446(9) 0.24028(9) 0.0293(4) Uani 1 1 d . . . . .
C62 C 0.7928(3) 0.60154(10) 0.06266(10) 0.0302(4) Uani 1 1 d . . . . .
H62 H 0.791648 0.602522 0.115311 0.036 Uiso 1 1 calc R U . . .
C61 C 0.8258(3) 0.67180(10) 0.02866(10) 0.0322(4) Uani 1 1 d . . . . .
H61 H 0.849437 0.721740 0.058051 0.039 Uiso 1 1 calc R U . . .
C12 C 0.7703(3) -0.02257(9) 0.13516(9) 0.0296(4) Uani 1 1 d . . . . .
C43 C 0.7616(2) -0.01007(10) 0.57294(9) 0.0287(3) Uani 1 1 d . . . . .
C52 C 0.6607(3) 0.31346(10) 0.05180(11) 0.0331(4) Uani 1 1 d . . . . .
H52 H 0.668663 0.316617 0.104739 0.040 Uiso 1 1 calc R U . . .
C60 C 0.8255(3) 0.67140(10) -0.04978(11) 0.0340(4) Uani 1 1 d . . . . .
H60 H 0.848561 0.721037 -0.072368 0.041 Uiso 1 1 calc R U . . .
C17 C 0.9249(3) -0.05841(10) 0.16602(10) 0.0332(4) Uani 1 1 d . . . . .
H17 H 0.960050 -0.052002 0.218398 0.040 Uiso 1 1 calc R U . . .
C59 C 0.7925(3) 0.60084(10) -0.09321(10) 0.0324(4) Uani 1 1 d . . . . .
H59 H 0.792938 0.601537 -0.145794 0.039 Uiso 1 1 calc R U . . .
C44 C 0.8195(3) 0.07076(11) 0.59891(9) 0.0311(4) Uani 1 1 d . . . . .
H44 H 0.840131 0.084917 0.651115 0.037 Uiso 1 1 calc R U . . .
C9 C 0.6108(3) -0.01239(10) 0.25642(10) 0.0326(4) Uani 1 1 d . . . . .
C18 C 0.7478(3) 0.11498(10) 0.19928(10) 0.0329(4) Uani 1 1 d . . . . .
C48 C 0.8905(3) 0.24773(10) 0.44533(11) 0.0340(4) Uani 1 1 d . . . . .
H48 H 0.903447 0.287988 0.410715 0.041 Uiso 1 1 calc R U . . .
C40 C 0.6403(3) -0.16983(11) 0.51290(11) 0.0340(4) Uani 1 1 d . . . . .
H40 H 0.597882 -0.224251 0.493519 0.041 Uiso 1 1 calc R U . . .
C31 C 0.7471(3) 0.46172(11) 0.42976(10) 0.0345(4) Uani 1 1 d . . . . .
H31 H 0.883326 0.480759 0.449269 0.041 Uiso 1 1 calc R U . . .
C19 C 0.9545(3) 0.14131(11) 0.19936(11) 0.0373(4) Uani 1 1 d . . . . .
H19 H 1.038908 0.104196 0.185926 0.045 Uiso 1 1 calc R U . . .
C33 C 0.8609(3) 0.66985(10) 0.25838(10) 0.0371(4) Uani 1 1 d . . . . .
H33 H 0.974440 0.654901 0.236996 0.044 Uiso 1 1 calc R U . . .
C37 C 0.5865(3) 0.64119(11) 0.33389(10) 0.0384(4) Uani 1 1 d . . . . .
H37 H 0.508689 0.606441 0.364221 0.046 Uiso 1 1 calc R U . . .
C11 C 0.6477(3) 0.02682(10) 0.18165(10) 0.0313(4) Uani 1 1 d . . . . .
C46 C 0.9040(3) 0.21490(11) 0.57365(11) 0.0348(4) Uani 1 1 d . . . . .
H46 H 0.927504 0.231309 0.625410 0.042 Uiso 1 1 calc R U . . .
C16 C 1.0287(3) -0.10346(10) 0.12119(11) 0.0367(4) Uani 1 1 d . . . . .
H16 H 1.133878 -0.127750 0.143189 0.044 Uiso 1 1 calc R U . . .
C42 C 0.7298(3) -0.07411(11) 0.62071(10) 0.0352(4) Uani 1 1 d . . . . .
H42 H 0.749672 -0.062734 0.673292 0.042 Uiso 1 1 calc R U . . .
C13 C 0.7242(3) -0.03307(12) 0.05803(10) 0.0398(4) Uani 1 1 d . . . . .
H13 H 0.619265 -0.008953 0.035607 0.048 Uiso 1 1 calc R U . . .
C27 C 0.4813(3) 0.45185(11) 0.33231(10) 0.0378(4) Uani 1 1 d . . . . .
H27 H 0.433318 0.463902 0.284048 0.045 Uiso 1 1 calc R U . . .
C53 C 0.6174(3) 0.24046(11) 0.01168(12) 0.0383(4) Uani 1 1 d . . . . .
H53 H 0.594621 0.192689 0.037178 0.046 Uiso 1 1 calc R U . . .
C55 C 0.6421(3) 0.30212(11) -0.10533(11) 0.0364(4) Uani 1 1 d . . . . .
H55 H 0.637856 0.297286 -0.158197 0.044 Uiso 1 1 calc R U . . .
C47 C 0.9242(3) 0.27114(10) 0.52290(11) 0.0371(4) Uani 1 1 d . . . . .
H47 H 0.961122 0.326610 0.539474 0.045 Uiso 1 1 calc R U . . .
C41 C 0.6711(3) -0.15160(11) 0.59123(11) 0.0373(4) Uani 1 1 d . . . . .
H41 H 0.650549 -0.193946 0.623525 0.045 Uiso 1 1 calc R U . . .
C54 C 0.6056(3) 0.23449(11) -0.06736(12) 0.0392(4) Uani 1 1 d . . . . .
H54 H 0.572102 0.183022 -0.094125 0.047 Uiso 1 1 calc R U . . .
C29 C 0.4194(3) 0.38583(11) 0.44476(12) 0.0449(5) Uani 1 1 d . . . . .
H29 H 0.330340 0.354014 0.473864 0.054 Uiso 1 1 calc R U . . .
C14 C 0.8282(3) -0.07794(12) 0.01356(11) 0.0455(5) Uani 1 1 d . . . . .
H14 H 0.794031 -0.084265 -0.038875 0.055 Uiso 1 1 calc R U . . .
C30 C 0.6169(3) 0.41390(12) 0.47189(11) 0.0437(5) Uani 1 1 d . . . . .
H30 H 0.665214 0.400665 0.519681 0.052 Uiso 1 1 calc R U . . .
C23 C 0.6275(3) 0.17047(11) 0.21957(11) 0.0420(5) Uani 1 1 d . . . . .
H23 H 0.486017 0.153234 0.220095 0.050 Uiso 1 1 calc R U . . .
C15 C 0.9804(3) -0.11339(11) 0.04447(11) 0.0413(5) Uani 1 1 d . . . . .
H15 H 1.051588 -0.144277 0.013863 0.050 Uiso 1 1 calc R U . . .
C20 C 1.0391(4) 0.22202(11) 0.21909(12) 0.0459(5) Uani 1 1 d . . . . .
H20 H 1.180712 0.239523 0.219075 0.055 Uiso 1 1 calc R U . . .
C28 C 0.3512(3) 0.40442(12) 0.37445(12) 0.0452(5) Uani 1 1 d . . . . .
H28 H 0.215215 0.384703 0.354972 0.054 Uiso 1 1 calc R U . . .
C34 C 0.8072(4) 0.74396(11) 0.24528(11) 0.0489(6) Uani 1 1 d . . . . .
H34 H 0.882787 0.778573 0.214215 0.059 Uiso 1 1 calc R U . . .
C22 C 0.7124(4) 0.25101(12) 0.23911(12) 0.0495(5) Uani 1 1 d . . . . .
H22 H 0.628472 0.288236 0.252758 0.059 Uiso 1 1 calc R U . . .
C21 C 0.9172(4) 0.27680(11) 0.23872(11) 0.0478(5) Uani 1 1 d . . . . .
H21 H 0.974810 0.331754 0.251801 0.057 Uiso 1 1 calc R U . . .
C36 C 0.5360(4) 0.71638(12) 0.32091(12) 0.0507(6) Uani 1 1 d . . . . .
H36 H 0.424394 0.732375 0.342817 0.061 Uiso 1 1 calc R U . . .
C35 C 0.6465(4) 0.76763(11) 0.27663(12) 0.0544(6) Uani 1 1 d . . . . .
H35 H 0.611619 0.818627 0.268037 0.065 Uiso 1 1 calc R U . . .
H8 H 0.726(4) 0.4602(16) 0.1114(16) 0.076(8) Uiso 1 1 d . . . . .
H7 H 0.743(4) 0.0125(15) 0.3902(15) 0.069(8) Uiso 1 1 d . . . . .
H6 H 1.099(4) 0.5298(16) 0.3271(16) 0.075(9) Uiso 1 1 d . . . . .
H3 H 0.370(4) -0.0092(18) 0.1651(17) 0.078(9) Uiso 1 1 d . . . . .
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
C25 O6 H6 102.8(17) . . ?
C11 O3 H3 104.1(19) . . ?
C50 N7 C38 122.44(14) . . ?
C50 N7 H7 120.5(14) . . ?
C38 N7 H7 117.0(14) . . ?
C63 N8 C51 122.16(14) . . ?
C63 N8 H8 118.7(14) . . ?
C51 N8 H8 119.1(14) . . ?
N8 C63 C58 120.32(14) . . ?
N8 C63 C62 119.61(15) . . ?
C62 C63 C58 120.06(15) . . ?
C57 C58 C63 118.17(15) . . ?
C57 C58 C59 123.52(16) . . ?
C59 C58 C63 118.31(15) . . ?
C31 C26 C25 120.01(16) . . ?
C31 C26 C27 118.18(16) . . ?
C27 C26 C25 121.77(15) . . ?
N7 C50 C49 119.88(15) . . ?
N7 C50 C45 119.68(15) . . ?
C49 C50 C45 120.44(15) . . ?
N7 C38 C39 119.43(15) . . ?
N7 C38 C43 120.04(15) . . ?
C39 C38 C43 120.53(15) . . ?
N8 C51 C56 119.82(15) . . ?
N8 C51 C52 119.65(15) . . ?
C52 C51 C56 120.52(15) . . ?
C58 C57 H57 119.5 . . ?
C56 C57 C58 120.94(15) . . ?
C56 C57 H57 119.5 . . ?
C38 C39 H39 120.5 . . ?
C40 C39 C38 118.94(16) . . ?
C40 C39 H39 120.5 . . ?
C50 C49 H49 120.5 . . ?
C48 C49 C50 118.92(16) . . ?
C48 C49 H49 120.5 . . ?
C33 C32 C25 117.68(16) . . ?
C37 C32 C25 123.99(15) . . ?
C37 C32 C33 118.26(16) . . ?
C50 C45 C46 118.25(16) . . ?
C44 C45 C50 118.52(15) . . ?
C44 C45 C46 123.22(16) . . ?
C57 C56 C51 118.58(15) . . ?
C57 C56 C55 123.31(16) . . ?
C55 C56 C51 118.10(16) . . ?
O6 C25 C26 110.13(13) . . ?
O6 C25 C32 107.14(13) . . ?
O6 C25 C24 107.18(13) . . ?
C26 C25 C24 109.71(13) . . ?
C32 C25 C26 113.40(14) . . ?
C32 C25 C24 109.06(13) . . ?
O4 C24 C25 116.80(15) . . ?
O5 C24 O4 126.63(16) . . ?
O5 C24 C25 116.56(16) . . ?
C63 C62 H62 120.2 . . ?
C61 C62 C63 119.54(16) . . ?
C61 C62 H62 120.2 . . ?
C62 C61 H61 119.5 . . ?
C62 C61 C60 120.94(16) . . ?
C60 C61 H61 119.5 . . ?
C17 C12 C11 123.29(15) . . ?
C17 C12 C13 117.85(17) . . ?
C13 C12 C11 118.86(16) . . ?
C44 C43 C38 118.11(15) . . ?
C44 C43 C42 123.52(16) . . ?
C42 C43 C38 118.37(16) . . ?
C51 C52 H52 120.4 . . ?
C53 C52 C51 119.13(17) . . ?
C53 C52 H52 120.4 . . ?
C61 C60 H60 119.6 . . ?
C59 C60 C61 120.80(16) . . ?
C59 C60 H60 119.6 . . ?
C12 C17 H17 119.6 . . ?
C16 C17 C12 120.72(17) . . ?
C16 C17 H17 119.6 . . ?
C58 C59 H59 119.8 . . ?
C60 C59 C58 120.33(16) . . ?
C60 C59 H59 119.8 . . ?
C45 C44 C43 121.20(15) . . ?
C45 C44 H44 119.4 . . ?
C43 C44 H44 119.4 . . ?
O1 C9 C11 116.01(15) . . ?
O2 C9 O1 127.09(17) . . ?
O2 C9 C11 116.90(17) . . ?
C19 C18 C11 122.80(16) . . ?
C19 C18 C23 118.69(17) . . ?
C23 C18 C11 118.43(17) . . ?
C49 C48 H48 119.3 . . ?
C49 C48 C47 121.34(17) . . ?
C47 C48 H48 119.3 . . ?
C39 C40 H40 119.4 . . ?
C39 C40 C41 121.19(17) . . ?
C41 C40 H40 119.4 . . ?
C26 C31 H31 119.5 . . ?
C26 C31 C30 120.93(18) . . ?
C30 C31 H31 119.5 . . ?
C18 C19 H19 119.8 . . ?
C18 C19 C20 120.39(19) . . ?
C20 C19 H19 119.8 . . ?
C32 C33 H33 119.6 . . ?
C34 C33 C32 120.8(2) . . ?
C34 C33 H33 119.6 . . ?
C32 C37 H37 119.9 . . ?
C32 C37 C36 120.27(19) . . ?
C36 C37 H37 119.9 . . ?
O3 C11 C12 109.18(14) . . ?
O3 C11 C9 107.65(14) . . ?
O3 C11 C18 107.62(14) . . ?
C12 C11 C9 109.58(13) . . ?
C18 C11 C12 113.85(14) . . ?
C18 C11 C9 108.77(14) . . ?
C45 C46 H46 119.8 . . ?
C47 C46 C45 120.46(17) . . ?
C47 C46 H46 119.8 . . ?
C17 C16 H16 119.7 . . ?
C17 C16 C15 120.61(18) . . ?
C15 C16 H16 119.7 . . ?
C43 C42 H42 119.9 . . ?
C41 C42 C43 120.19(17) . . ?
C41 C42 H42 119.9 . . ?
C12 C13 H13 119.4 . . ?
C14 C13 C12 121.23(19) . . ?
C14 C13 H13 119.4 . . ?
C26 C27 H27 119.6 . . ?
C26 C27 C28 120.87(18) . . ?
C28 C27 H27 119.6 . . ?
C52 C53 H53 119.4 . . ?
C52 C53 C54 121.27(18) . . ?
C54 C53 H53 119.4 . . ?
C56 C55 H55 119.8 . . ?
C54 C55 C56 120.38(18) . . ?
C54 C55 H55 119.8 . . ?
C48 C47 H47 119.7 . . ?
C46 C47 C48 120.57(16) . . ?
C46 C47 H47 119.7 . . ?
C40 C41 H41 119.6 . . ?
C42 C41 C40 120.78(16) . . ?
C42 C41 H41 119.6 . . ?
C53 C54 H54 119.7 . . ?
C55 C54 C53 120.56(17) . . ?
C55 C54 H54 119.7 . . ?
C30 C29 H29 120.3 . . ?
C30 C29 C28 119.31(18) . . ?
C28 C29 H29 120.3 . . ?
C13 C14 H14 119.7 . . ?
C15 C14 C13 120.59(18) . . ?
C15 C14 H14 119.7 . . ?
C31 C30 H30 119.8 . . ?
C29 C30 C31 120.46(18) . . ?
C29 C30 H30 119.8 . . ?
C18 C23 H23 119.6 . . ?
C18 C23 C22 120.8(2) . . ?
C22 C23 H23 119.6 . . ?
C16 C15 H15 120.5 . . ?
C14 C15 C16 119.00(18) . . ?
C14 C15 H15 120.5 . . ?
C19 C20 H20 119.9 . . ?
C21 C20 C19 120.3(2) . . ?
C21 C20 H20 119.9 . . ?
C27 C28 H28 119.9 . . ?
C29 C28 C27 120.2(2) . . ?
C29 C28 H28 119.9 . . ?
C33 C34 H34 119.6 . . ?
C35 C34 C33 120.78(19) . . ?
C35 C34 H34 119.6 . . ?
C23 C22 H22 119.9 . . ?
C21 C22 C23 120.2(2) . . ?
C21 C22 H22 119.9 . . ?
C20 C21 H21 120.2 . . ?
C22 C21 C20 119.61(18) . . ?
C22 C21 H21 120.2 . . ?
C37 C36 H36 119.6 . . ?
C35 C36 C37 120.8(2) . . ?
C35 C36 H36 119.6 . . ?
C34 C35 C36 119.13(18) . . ?
C34 C35 H35 120.4 . . ?
C36 C35 H35 120.4 . . ?
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
O6 C25 1.427(2) . ?
O6 H6 0.96(3) . ?
O1 C9 1.269(2) . ?
O4 C24 1.269(2) . ?
O3 C11 1.428(2) . ?
O3 H3 0.90(3) . ?
O5 C24 1.235(2) . ?
N7 C50 1.3518(19) . ?
N7 C38 1.358(2) . ?
N7 H7 1.04(3) . ?
N8 C63 1.352(2) . ?
N8 C51 1.356(2) . ?
N8 H8 1.06(3) . ?
O2 C9 1.240(2) . ?
C63 C58 1.428(2) . ?
C63 C62 1.415(2) . ?
C58 C57 1.399(2) . ?
C58 C59 1.423(2) . ?
C26 C25 1.529(2) . ?
C26 C31 1.385(2) . ?
C26 C27 1.391(2) . ?
C50 C49 1.420(2) . ?
C50 C45 1.426(2) . ?
C38 C39 1.419(2) . ?
C38 C43 1.424(2) . ?
C51 C56 1.432(2) . ?
C51 C52 1.416(2) . ?
C57 H57 0.9500 . ?
C57 C56 1.391(2) . ?
C39 H39 0.9500 . ?
C39 C40 1.365(2) . ?
C49 H49 0.9500 . ?
C49 C48 1.369(2) . ?
C32 C25 1.528(2) . ?
C32 C33 1.396(2) . ?
C32 C37 1.388(2) . ?
C45 C44 1.394(2) . ?
C45 C46 1.430(2) . ?
C56 C55 1.423(2) . ?
C25 C24 1.559(2) . ?
C62 H62 0.9500 . ?
C62 C61 1.363(2) . ?
C61 H61 0.9500 . ?
C61 C60 1.415(3) . ?
C12 C17 1.388(3) . ?
C12 C11 1.533(2) . ?
C12 C13 1.394(2) . ?
C43 C44 1.394(2) . ?
C43 C42 1.424(2) . ?
C52 H52 0.9500 . ?
C52 C53 1.364(2) . ?
C60 H60 0.9500 . ?
C60 C59 1.360(2) . ?
C17 H17 0.9500 . ?
C17 C16 1.387(2) . ?
C59 H59 0.9500 . ?
C44 H44 0.9500 . ?
C9 C11 1.560(2) . ?
C18 C19 1.389(3) . ?
C18 C11 1.528(2) . ?
C18 C23 1.392(3) . ?
C48 H48 0.9500 . ?
C48 C47 1.419(3) . ?
C40 H40 0.9500 . ?
C40 C41 1.418(3) . ?
C31 H31 0.9500 . ?
C31 C30 1.395(3) . ?
C19 H19 0.9500 . ?
C19 C20 1.397(2) . ?
C33 H33 0.9500 . ?
C33 C34 1.391(3) . ?
C37 H37 0.9500 . ?
C37 C36 1.399(3) . ?
C46 H46 0.9500 . ?
C46 C47 1.359(3) . ?
C16 H16 0.9500 . ?
C16 C15 1.389(3) . ?
C42 H42 0.9500 . ?
C42 C41 1.362(3) . ?
C13 H13 0.9500 . ?
C13 C14 1.383(3) . ?
C27 H27 0.9500 . ?
C27 C28 1.391(3) . ?
C53 H53 0.9500 . ?
C53 C54 1.418(3) . ?
C55 H55 0.9500 . ?
C55 C54 1.366(3) . ?
C47 H47 0.9500 . ?
C41 H41 0.9500 . ?
C54 H54 0.9500 . ?
C29 H29 0.9500 . ?
C29 C30 1.373(3) . ?
C29 C28 1.387(3) . ?
C14 H14 0.9500 . ?
C14 C15 1.372(3) . ?
C30 H30 0.9500 . ?
C23 H23 0.9500 . ?
C23 C22 1.394(3) . ?
C15 H15 0.9500 . ?
C20 H20 0.9500 . ?
C20 C21 1.388(3) . ?
C28 H28 0.9500 . ?
C34 H34 0.9500 . ?
C34 C35 1.370(3) . ?
C22 H22 0.9500 . ?
C22 C21 1.376(3) . ?
C21 H21 0.9500 . ?
C36 H36 0.9500 . ?
C36 C35 1.381(3) . ?
C35 H35 0.9500 . ?
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
O6 C25 C24 O4 -174.12(13) . . . . ?
O6 C25 C24 O5 4.92(19) . . . . ?
O1 C9 C11 O3 -164.87(14) . . . . ?
O1 C9 C11 C12 76.50(18) . . . . ?
O1 C9 C11 C18 -48.5(2) . . . . ?
N7 C50 C49 C48 178.42(15) . . . . ?
N7 C50 C45 C44 -0.6(2) . . . . ?
N7 C50 C45 C46 -179.55(15) . . . . ?
N7 C38 C39 C40 -179.80(15) . . . . ?
N7 C38 C43 C44 1.0(2) . . . . ?
N7 C38 C43 C42 -179.69(14) . . . . ?
N8 C63 C58 C57 0.6(2) . . . . ?
N8 C63 C58 C59 -179.51(15) . . . . ?
N8 C63 C62 C61 179.48(15) . . . . ?
N8 C51 C56 C57 1.1(2) . . . . ?
N8 C51 C56 C55 -177.83(15) . . . . ?
N8 C51 C52 C53 177.36(15) . . . . ?
O2 C9 C11 O3 15.9(2) . . . . ?
O2 C9 C11 C12 -102.76(18) . . . . ?
O2 C9 C11 C18 132.20(17) . . . . ?
C63 N8 C51 C56 -0.8(2) . . . . ?
C63 N8 C51 C52 -179.57(15) . . . . ?
C63 C58 C57 C56 -0.2(2) . . . . ?
C63 C58 C59 C60 -0.8(2) . . . . ?
C63 C62 C61 C60 0.8(3) . . . . ?
C58 C63 C62 C61 -1.4(2) . . . . ?
C58 C57 C56 C51 -0.6(2) . . . . ?
C58 C57 C56 C55 178.28(16) . . . . ?
C26 C25 C24 O4 66.31(18) . . . . ?
C26 C25 C24 O5 -114.64(16) . . . . ?
C26 C31 C30 C29 -0.1(3) . . . . ?
C26 C27 C28 C29 -0.5(3) . . . . ?
C50 N7 C38 C39 179.11(14) . . . . ?
C50 N7 C38 C43 -1.5(2) . . . . ?
C50 C49 C48 C47 1.8(3) . . . . ?
C50 C45 C44 C43 0.2(2) . . . . ?
C50 C45 C46 C47 0.5(3) . . . . ?
C38 N7 C50 C49 -178.61(15) . . . . ?
C38 N7 C50 C45 1.3(2) . . . . ?
C38 C39 C40 C41 -1.0(3) . . . . ?
C38 C43 C44 C45 -0.4(2) . . . . ?
C38 C43 C42 C41 0.0(3) . . . . ?
C51 N8 C63 C58 -0.1(2) . . . . ?
C51 N8 C63 C62 178.95(15) . . . . ?
C51 C56 C55 C54 0.7(3) . . . . ?
C51 C52 C53 C54 0.2(3) . . . . ?
C57 C58 C59 C60 179.10(16) . . . . ?
C57 C56 C55 C54 -178.19(17) . . . . ?
C39 C38 C43 C44 -179.60(15) . . . . ?
C39 C38 C43 C42 -0.3(2) . . . . ?
C39 C40 C41 C42 0.7(3) . . . . ?
C49 C50 C45 C44 179.27(15) . . . . ?
C49 C50 C45 C46 0.3(2) . . . . ?
C49 C48 C47 C46 -0.9(3) . . . . ?
C32 C25 C24 O4 -58.45(19) . . . . ?
C32 C25 C24 O5 120.60(16) . . . . ?
C32 C33 C34 C35 1.3(3) . . . . ?
C32 C37 C36 C35 0.4(3) . . . . ?
C45 C50 C49 C48 -1.5(2) . . . . ?
C45 C46 C47 C48 -0.3(3) . . . . ?
C56 C51 C52 C53 -1.4(2) . . . . ?
C56 C55 C54 C53 -1.9(3) . . . . ?
C25 C26 C31 C30 176.60(16) . . . . ?
C25 C26 C27 C28 -176.31(17) . . . . ?
C25 C32 C33 C34 -177.99(16) . . . . ?
C25 C32 C37 C36 176.99(17) . . . . ?
C62 C63 C58 C57 -178.44(15) . . . . ?
C62 C63 C58 C59 1.4(2) . . . . ?
C62 C61 C60 C59 -0.1(3) . . . . ?
C61 C60 C59 C58 0.1(3) . . . . ?
C12 C17 C16 C15 0.2(3) . . . . ?
C12 C13 C14 C15 0.0(3) . . . . ?
C43 C38 C39 C40 0.8(2) . . . . ?
C43 C42 C41 C40 -0.1(3) . . . . ?
C52 C51 C56 C57 179.92(15) . . . . ?
C52 C51 C56 C55 1.0(2) . . . . ?
C52 C53 C54 C55 1.5(3) . . . . ?
C17 C12 C11 O3 -155.19(16) . . . . ?
C17 C12 C11 C9 -37.5(2) . . . . ?
C17 C12 C11 C18 84.5(2) . . . . ?
C17 C12 C13 C14 0.2(3) . . . . ?
C17 C16 C15 C14 0.0(3) . . . . ?
C59 C58 C57 C56 179.92(16) . . . . ?
C44 C45 C46 C47 -178.34(17) . . . . ?
C44 C43 C42 C41 179.23(16) . . . . ?
C18 C19 C20 C21 -0.1(3) . . . . ?
C18 C23 C22 C21 -0.1(3) . . . . ?
C31 C26 C25 O6 3.5(2) . . . . ?
C31 C26 C25 C32 -116.59(17) . . . . ?
C31 C26 C25 C24 121.20(17) . . . . ?
C31 C26 C27 C28 1.4(3) . . . . ?
C19 C18 C11 O3 -144.34(17) . . . . ?
C19 C18 C11 C12 -23.2(2) . . . . ?
C19 C18 C11 C9 99.30(19) . . . . ?
C19 C18 C23 C22 0.4(3) . . . . ?
C19 C20 C21 C22 0.4(3) . . . . ?
C33 C32 C25 O6 63.25(18) . . . . ?
C33 C32 C25 C26 -175.02(15) . . . . ?
C33 C32 C25 C24 -52.4(2) . . . . ?
C33 C32 C37 C36 0.0(3) . . . . ?
C33 C34 C35 C36 -0.8(3) . . . . ?
C37 C32 C25 O6 -113.72(18) . . . . ?
C37 C32 C25 C26 8.0(2) . . . . ?
C37 C32 C25 C24 130.58(17) . . . . ?
C37 C32 C33 C34 -0.8(3) . . . . ?
C37 C36 C35 C34 0.0(3) . . . . ?
C11 C12 C17 C16 179.03(15) . . . . ?
C11 C12 C13 C14 -179.15(17) . . . . ?
C11 C18 C19 C20 -177.18(17) . . . . ?
C11 C18 C23 C22 177.42(17) . . . . ?
C46 C45 C44 C43 179.08(16) . . . . ?
C42 C43 C44 C45 -179.66(16) . . . . ?
C13 C12 C17 C16 -0.3(3) . . . . ?
C13 C12 C11 O3 24.2(2) . . . . ?
C13 C12 C11 C9 141.84(16) . . . . ?
C13 C12 C11 C18 -96.11(19) . . . . ?
C13 C14 C15 C16 -0.1(3) . . . . ?
C27 C26 C25 O6 -178.88(15) . . . . ?
C27 C26 C25 C32 61.1(2) . . . . ?
C27 C26 C25 C24 -61.1(2) . . . . ?
C27 C26 C31 C30 -1.1(3) . . . . ?
C30 C29 C28 C27 -0.8(3) . . . . ?
C23 C18 C19 C20 -0.3(3) . . . . ?
C23 C18 C11 O3 38.8(2) . . . . ?
C23 C18 C11 C12 159.96(16) . . . . ?
C23 C18 C11 C9 -77.5(2) . . . . ?
C23 C22 C21 C20 -0.3(3) . . . . ?
C28 C29 C30 C31 1.0(3) . . . . ?
