#------------------------------------------------------------------------------
#$Date: 2022-08-09 02:11:49 +0300 (Tue, 09 Aug 2022) $
#$Revision: 277157 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/71/09/7710916.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_7710916
loop_
_publ_author_name
'Mitzel, Norbert Werner'
'Aders, Niklas'
'Lamm, Jan-Hendrik'
'Beckmann, Jean Louis'
'Neumann, Beate'
'Stammler, Georg'
_publ_section_title
;
 Synthesis of bi- and tetradentate poly-Lewis acids by hydroalumination of
 poly-alkynyl-anthracene derivatives
;
_journal_name_full               'Dalton Transactions'
_journal_paper_doi               10.1039/D2DT02118H
_journal_year                    2022
_chemical_formula_moiety         'C48 H44 O4, (C3 H7 N1 O1)'
_chemical_formula_sum            'C51 H51 N O5'
_chemical_formula_weight         757.92
_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             2022-01-27
_audit_creation_method
;
Olex2 1.3-ac4
(compiled 2019.04.23 svn.r3594 for Rigaku Oxford Diffraction, GUI svn.r5739)
;
_audit_update_record
;
2022-04-01 deposited with the CCDC.	2022-08-08 downloaded from the CCDC.
;
_cell_angle_alpha                92.036(5)
_cell_angle_beta                 102.618(5)
_cell_angle_gamma                114.109(6)
_cell_formula_units_Z            1
_cell_length_a                   9.8534(6)
_cell_length_b                   10.8417(7)
_cell_length_c                   11.1079(6)
_cell_measurement_reflns_used    4045
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      75.9760
_cell_measurement_theta_min      4.1150
_cell_volume                     1046.54(12)
_computing_cell_refinement       'CrysAlisPro 1.171.41.122a (Rigaku OD, 2021)'
_computing_data_collection       'CrysAlisPro 1.171.41.122a (Rigaku OD, 2021)'
_computing_data_reduction        'CrysAlisPro 1.171.41.122a (Rigaku OD, 2021)'
_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      100.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.3114
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.971
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω   -110.00 -18.00   1.00   33.00    --  -38.50 -37.00   0.00   92
  2  ω     -6.00  32.00   1.00   33.00    --  -38.50  37.00-180.00   38
  3  ω    -23.00  43.00   1.00   33.00    --   41.95 -57.00-150.00   66
  4  ω    -19.00 106.00   1.00   33.00    --   41.95   0.00   0.00  125
  5  ω     29.00  82.00   1.00   33.00    --   41.95-125.00-180.00   53
  6  ω     29.00  91.00   1.00   33.00    --   41.95-125.00   0.00   62
  7  ω     90.00 134.00   1.00   54.00    --  111.00 -61.00-120.00   44
  8  ω     42.00 126.00   1.00   54.00    --  111.00 -45.00  30.00   84
  9  ω    105.00 133.00   1.00   54.00    --  111.00 -77.00 150.00   28
 10  ω     41.00  74.00   1.00   54.00    --  111.00-125.00   0.00   33
 11  ω     84.00 112.00   1.00   54.00    --  111.00-125.00   0.00   28
 12  ω     63.00 107.00   1.00   54.00    --  111.00 -94.00  90.00   44
 13  ω     66.00 113.00   1.00   54.00    --  111.00-125.00-150.00   47
 14  ω    109.00 161.00   1.00   54.00    --  111.00  77.00  60.00   52
 15  ω    101.00 129.00   1.00   54.00    --  111.00  30.00-150.00   28
 16  ω     55.00 112.00   1.00   54.00    --  111.00-125.00  60.00   57
 17  ω     41.00 112.00   1.00   54.00    --  111.00 -30.00 150.00   71
 18  ω     35.00 100.00   1.00   54.00    --  111.00 -94.00-150.00   65
 19  ω    112.00 176.00   1.00   54.00    --  111.00  77.00 -60.00   64
 20  ω    127.00 178.00   1.00   54.00    --  111.00  77.00-180.00   51
 21  ω     42.00 113.00   1.00   54.00    --  111.00-125.00 -30.00   71
 22  ω     98.00 159.00   1.00   54.00    --  111.00  45.00 120.00   61
 23  ω     55.00 106.00   1.00   54.00    --  111.00 -15.00 -90.00   51
 24  ω    122.00 150.00   1.00   54.00    --  111.00 -15.00 -90.00   28
 25  ω     71.00 112.00   1.00   54.00    --  111.00-125.00  90.00   41
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0446079000
_diffrn_orient_matrix_UB_12      -0.0052716000
_diffrn_orient_matrix_UB_13      0.1409309000
_diffrn_orient_matrix_UB_21      -0.1709124000
_diffrn_orient_matrix_UB_22      -0.0593007000
_diffrn_orient_matrix_UB_23      0.0009595000
_diffrn_orient_matrix_UB_31      -0.0136672000
_diffrn_orient_matrix_UB_32      -0.1455181000
_diffrn_orient_matrix_UB_33      -0.0272188000
_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  0.0391
_diffrn_reflns_av_unetI/netI     0.0427
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.971
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            12900
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.971
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         76.474
_diffrn_reflns_theta_min         4.119
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.603
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.697
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.41.122a (Rigaku Oxford Diffraction, 2021)
Numerical absorption correction based on gaussian integration over
a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.203
_exptl_crystal_description       needle
_exptl_crystal_F_000             404
_exptl_crystal_size_max          0.34
_exptl_crystal_size_mid          0.04
_exptl_crystal_size_min          0.02
_refine_diff_density_max         0.357
_refine_diff_density_min         -0.265
_refine_diff_density_rms         0.059
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.937
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     365
_refine_ls_number_reflns         8016
_refine_ls_number_restraints     7
_refine_ls_restrained_S_all      0.939
_refine_ls_R_factor_all          0.0744
_refine_ls_R_factor_gt           0.0552
_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)+(0.1098P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1444
_refine_ls_wR_factor_ref         0.1530
_reflns_Friedel_coverage         0.000
_reflns_number_gt                5607
_reflns_number_total             8016
_reflns_threshold_expression     'I > 2σ(I)'
_twin_special_details
;
Component 2 rotated by 2.4698° 
around [0.39 0.77 -0.50] (reciprocal) or [0.63 0.76 -0.18] (direct)
;
_cod_data_source_file            d2dt02118h2.cif
_cod_data_source_block           syn-6
_cod_database_code               7710916
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C51 H51  N O5'
_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   0.988
_shelx_estimated_absorpt_t_min   0.821
_olex2_refinement_description
;
1. Twinned data refinement
 Scales: 0.6396(14)
 0.3604(14)
2. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
3. Shared sites
{N1A, N1B}
4. Restrained distances
 N1A-C26A \\sim N1B-C27B \\sim N1A-C27A \\sim N1B-C26B
 with sigma of 0.02
 N1B-C25B \\sim N1A-C25A
 with sigma of 0.02
5. Uiso/Uaniso restraints and constraints
Uanis(N1A) = Uanis(N1B)
Uanis(C26B) = Uanis(C26A)
6. Others
 Sof(N1B)=Sof(C25B)=Sof(H25B)=Sof(C26B)=Sof(H26D)=Sof(H26E)=Sof(H26F)=
 Sof(C27B)=Sof(H27D)=Sof(H27E)=Sof(H27F)=0.5*(1-FVAR(2))
 Sof(N1A)=Sof(C25A)=Sof(H25A)=Sof(C26A)=Sof(H26A)=Sof(H26B)=Sof(H26C)=
 Sof(C27A)=Sof(H27A)=Sof(H27B)=Sof(H27C)=0.5*FVAR(2)
 Fixed Sof: O3(0.5)
7.a Me refined with riding coordinates:
 C26A(H26A,H26B,H26C), C27A(H27A,H27B,H27C), C26B(H26D,H26E,H26F), C27B(H27D,
 H27E,H27F)
7.b Aromatic/amide H refined with riding coordinates:
 C25A(H25A), C25B(H25B)
7.c Idealised tetrahedral OH refined as rotating group:
 O1(H1), O2(H2)
;
_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 2.690
_oxdiff_exptl_absorpt_empirical_full_min 0.441
_oxdiff_twin_integration_method  simultaneous
_oxdiff_twin_items               2
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 0.38223(15) 0.11527(14) -0.04543(12) 0.0263(3) Uani 1 1 d . . . . .
H1 H 0.340562 0.029917 -0.049384 0.039 Uiso 1 1 calc GR . . . .
O2 O 0.69590(15) 0.16766(13) 1.07788(12) 0.0261(3) Uani 1 1 d . . . . .
H2 H 0.610237 0.164560 1.041116 0.039 Uiso 1 1 calc GR . . . .
C1 C 0.2695(2) 0.12870(18) 0.35182(16) 0.0203(4) Uani 1 1 d . . . . .
C2 C 0.38755(19) 0.10477(17) 0.42868(15) 0.0184(3) Uani 1 1 d . . . . .
C3 C 0.50782(19) 0.07973(18) 0.38042(15) 0.0181(3) Uani 1 1 d . . . . .
H3 H 0.511(3) 0.109(2) 0.295(2) 0.022 Uiso 1 1 d R . . . .
C4 C 0.6628(2) 0.16624(18) 0.46918(16) 0.0190(4) Uani 1 1 d . . . . .
C5 C 0.7902(2) 0.24342(19) 0.42702(16) 0.0212(4) Uani 1 1 d . . . . .
H5 H 0.789(3) 0.244(2) 0.336(2) 0.025 Uiso 1 1 d R . . . .
C6 C 0.9309(2) 0.32213(19) 0.51286(18) 0.0238(4) Uani 1 1 d . . . . .
H6 H 1.020(3) 0.371(3) 0.485(2) 0.029 Uiso 1 1 d R . . . .
C7 C 0.9427(2) 0.32412(19) 0.63904(17) 0.0236(4) Uani 1 1 d . . . . .
H7 H 1.034(3) 0.378(3) 0.693(2) 0.028 Uiso 1 1 d R . . . .
C8 C 0.8138(2) 0.24769(18) 0.68277(16) 0.0198(4) Uani 1 1 d . . . . .
C9 C 0.67272(19) 0.16643(17) 0.59665(15) 0.0187(4) Uani 1 1 d . . . . .
C10 C 0.52814(19) 0.07988(18) 0.63428(15) 0.0183(3) Uani 1 1 d . . . . .
H10 H 0.538(3) 0.108(2) 0.722(2) 0.022 Uiso 1 1 d R . . . .
C11 C 0.39724(19) 0.10392(17) 0.55569(15) 0.0190(4) Uani 1 1 d . . . . .
C12 C 0.2894(2) 0.12356(19) 0.60658(16) 0.0217(4) Uani 1 1 d . . . . .
H12 H 0.298(3) 0.127(2) 0.700(2) 0.026 Uiso 1 1 d R . . . .
C13 C 0.1699(2) 0.1439(2) 0.52969(18) 0.0257(4) Uani 1 1 d . . . . .
H13 H 0.093(3) 0.158(3) 0.567(2) 0.031 Uiso 1 1 d R . . . .
C14 C 0.1606(2) 0.1471(2) 0.40411(17) 0.0245(4) Uani 1 1 d . . . . .
H14 H 0.077(3) 0.164(3) 0.350(2) 0.029 Uiso 1 1 d R . . . .
C15 C 0.26573(19) 0.13871(18) 0.22280(16) 0.0209(4) Uani 1 1 d . . . . .
C16 C 0.2716(2) 0.15013(18) 0.11662(16) 0.0213(4) Uani 1 1 d . . . . .
C17 C 0.2829(2) 0.17088(18) -0.01201(16) 0.0210(4) Uani 1 1 d . . . . .
C18 C 0.3563(3) 0.3234(2) -0.0193(2) 0.0331(5) Uani 1 1 d . . . . .
H18A H 0.457(4) 0.367(3) 0.041(3) 0.050 Uiso 1 1 d R . . . .
H18B H 0.282(4) 0.360(3) -0.004(3) 0.050 Uiso 1 1 d R . . . .
H18C H 0.376(4) 0.340(3) -0.102(3) 0.050 Uiso 1 1 d R . . . .
C19 C 0.1237(2) 0.1009(3) -0.10274(18) 0.0305(4) Uani 1 1 d . . . . .
H19A H 0.128(3) 0.116(3) -0.194(3) 0.046 Uiso 1 1 d R . . . .
H19B H 0.055(4) 0.136(3) -0.082(3) 0.046 Uiso 1 1 d R . . . .
H19C H 0.077(4) -0.004(3) -0.101(3) 0.046 Uiso 1 1 d R . . . .
C20 C 0.8229(2) 0.25670(18) 0.81355(16) 0.0214(4) Uani 1 1 d . . . . .
C21 C 0.8227(2) 0.26624(18) 0.92165(16) 0.0219(4) Uani 1 1 d . . . . .
C22 C 0.81683(19) 0.28591(18) 1.05247(16) 0.0204(4) Uani 1 1 d . . . . .
C23 C 0.7825(2) 0.4090(2) 1.07226(19) 0.0272(4) Uani 1 1 d . . . . .
H23A H 0.686(3) 0.401(3) 1.008(3) 0.041 Uiso 1 1 d R . . . .
H23B H 0.876(3) 0.496(3) 1.069(3) 0.041 Uiso 1 1 d R . . . .
H23C H 0.764(3) 0.415(3) 1.156(3) 0.041 Uiso 1 1 d R . . . .
C24 C 0.9691(2) 0.3066(2) 1.14093(18) 0.0282(4) Uani 1 1 d . . . . .
H24A H 0.965(3) 0.321(3) 1.227(3) 0.042 Uiso 1 1 d R . . . .
H24B H 1.059(4) 0.388(3) 1.122(3) 0.042 Uiso 1 1 d R . . . .
H24C H 0.997(3) 0.233(3) 1.129(2) 0.042 Uiso 1 1 d R . . . .
O3 O 0.3426(5) 0.4996(5) 0.6957(5) 0.0647(12) Uani 0.5 1 d . . P . .
N1A N 0.4958(15) 0.4955(12) 0.5645(10) 0.038(2) Uani 0.336(4) 1 d D . P A -1
C25A C 0.3739(9) 0.5079(8) 0.6001(7) 0.0397(17) Uani 0.336(4) 1 d D . P A -1
H25A H 0.305577 0.525800 0.536156 0.048 Uiso 0.336(4) 1 calc R . P A -1
C26A C 0.6092(9) 0.4875(8) 0.6664(10) 0.051(2) Uani 0.336(4) 1 d D . P A -1
H26A H 0.690887 0.479015 0.634770 0.077 Uiso 0.336(4) 1 calc R . P A -1
H26B H 0.653319 0.570306 0.727082 0.077 Uiso 0.336(4) 1 calc R . P A -1
H26C H 0.560677 0.407631 0.706578 0.077 Uiso 0.336(4) 1 calc R . P A -1
C27A C 0.531(3) 0.500(4) 0.448(2) 0.063(9) Uani 0.336(4) 1 d D . P A -1
H27A H 0.625967 0.488080 0.455295 0.094 Uiso 0.336(4) 1 calc R . P A -1
H27B H 0.446806 0.427608 0.386328 0.094 Uiso 0.336(4) 1 calc R . P A -1
H27C H 0.546488 0.589146 0.420704 0.094 Uiso 0.336(4) 1 calc R . P A -1
N1B N 0.4958(15) 0.4955(12) 0.5645(10) 0.038(2) Uani 0.164(4) 1 d D . P A -2
C25B C 0.448(2) 0.484(2) 0.6652(19) 0.067(6) Uani 0.164(4) 1 d D . P A -2
H25B H 0.506863 0.456525 0.729383 0.081 Uiso 0.164(4) 1 calc R . P A -2
C26B C 0.400(3) 0.527(3) 0.473(3) 0.051(2) Uani 0.164(4) 1 d D . P A -2
H26D H 0.436860 0.535586 0.397079 0.077 Uiso 0.164(4) 1 calc R . P A -2
H26E H 0.295259 0.453761 0.454626 0.077 Uiso 0.164(4) 1 calc R . P A -2
H26F H 0.399379 0.613017 0.501624 0.077 Uiso 0.164(4) 1 calc R . P A -2
C27B C 0.631(2) 0.482(3) 0.565(3) 0.057(7) Uani 0.164(4) 1 d D . P A -2
H27D H 0.652312 0.493100 0.483199 0.085 Uiso 0.164(4) 1 calc R . P A -2
H27E H 0.716831 0.551098 0.628610 0.085 Uiso 0.164(4) 1 calc R . P A -2
H27F H 0.618635 0.390601 0.584470 0.085 Uiso 0.164(4) 1 calc R . 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_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
0 1 0 0.0198
0 -1 0 0.0198
0 0 -1 0.0098
0 0 1 0.0098
2 -1 -1 0.1598
-2 1 1 0.1598
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
C17 O1 H1 109.5 . . ?
C22 O2 H2 109.5 . . ?
C2 C1 C15 119.55(15) . . ?
C14 C1 C2 119.16(16) . . ?
C14 C1 C15 121.25(15) . . ?
C1 C2 C3 123.13(15) . . ?
C11 C2 C1 119.63(15) . . ?
C11 C2 C3 117.23(14) . . ?
C2 C3 H3 111.1(12) . . ?
C2 C3 C10 111.67(14) . 2_656 ?
C4 C3 C2 107.60(13) . . ?
C4 C3 H3 108.0(13) . . ?
C4 C3 C10 111.96(12) . 2_656 ?
C10 C3 H3 106.5(12) 2_656 . ?
C5 C4 C3 121.93(15) . . ?
C5 C4 C9 120.86(16) . . ?
C9 C4 C3 117.21(16) . . ?
C4 C5 H5 123.3(14) . . ?
C4 C5 C6 119.75(17) . . ?
C6 C5 H5 116.9(14) . . ?
C5 C6 H6 120.4(15) . . ?
C7 C6 C5 120.19(17) . . ?
C7 C6 H6 119.3(15) . . ?
C6 C7 H7 118.9(16) . . ?
C6 C7 C8 120.51(16) . . ?
C8 C7 H7 120.5(15) . . ?
C7 C8 C9 119.44(16) . . ?
C7 C8 C20 120.65(16) . . ?
C9 C8 C20 119.84(16) . . ?
C4 C9 C8 119.23(16) . . ?
C4 C9 C10 117.32(15) . . ?
C8 C9 C10 123.45(15) . . ?
C3 C10 H10 106.8(13) 2_656 . ?
C9 C10 C3 112.18(13) . 2_656 ?
C9 C10 H10 110.5(14) . . ?
C9 C10 C11 107.79(14) . . ?
C11 C10 C3 111.41(13) . 2_656 ?
C11 C10 H10 108.1(12) . . ?
C2 C11 C10 117.36(14) . . ?
C12 C11 C2 120.62(15) . . ?
C12 C11 C10 122.02(15) . . ?
C11 C12 H12 121.2(13) . . ?
C11 C12 C13 119.72(16) . . ?
C13 C12 H12 119.0(13) . . ?
C12 C13 H13 119.2(14) . . ?
C14 C13 C12 120.17(16) . . ?
C14 C13 H13 120.7(14) . . ?
C1 C14 H14 119.3(14) . . ?
C13 C14 C1 120.67(15) . . ?
C13 C14 H14 120.0(13) . . ?
C16 C15 C1 176.25(17) . . ?
C15 C16 C17 177.40(19) . . ?
O1 C17 C16 109.98(13) . . ?
O1 C17 C18 107.10(15) . . ?
O1 C17 C19 109.30(14) . . ?
C16 C17 C18 109.18(15) . . ?
C16 C17 C19 110.20(15) . . ?
C18 C17 C19 111.03(16) . . ?
C17 C18 H18A 110.0(19) . . ?
C17 C18 H18B 106.8(18) . . ?
C17 C18 H18C 110.9(18) . . ?
H18A C18 H18B 113(2) . . ?
H18A C18 H18C 106(3) . . ?
H18B C18 H18C 110(2) . . ?
C17 C19 H19A 111.6(17) . . ?
C17 C19 H19B 110.8(18) . . ?
C17 C19 H19C 110.7(16) . . ?
H19A C19 H19B 108(2) . . ?
H19A C19 H19C 107(2) . . ?
H19B C19 H19C 109(2) . . ?
C21 C20 C8 175.90(17) . . ?
C20 C21 C22 175.30(17) . . ?
O2 C22 C21 109.95(14) . . ?
O2 C22 C23 108.60(14) . . ?
O2 C22 C24 108.51(15) . . ?
C21 C22 C23 108.75(15) . . ?
C21 C22 C24 110.23(14) . . ?
C23 C22 C24 110.79(15) . . ?
C22 C23 H23A 111.8(15) . . ?
C22 C23 H23B 109.4(15) . . ?
C22 C23 H23C 109.2(16) . . ?
H23A C23 H23B 111(2) . . ?
H23A C23 H23C 107(2) . . ?
H23B C23 H23C 108(2) . . ?
C22 C24 H24A 109.8(17) . . ?
C22 C24 H24B 110.2(16) . . ?
C22 C24 H24C 113.2(17) . . ?
H24A C24 H24B 111(2) . . ?
H24A C24 H24C 110(2) . . ?
H24B C24 H24C 102(2) . . ?
C25A N1A C26A 113.9(8) . . ?
C25A N1A C27A 130.7(9) . . ?
C27A N1A C26A 115.2(9) . . ?
O3 C25A N1A 130.2(8) . . ?
O3 C25A H25A 114.9 . . ?
N1A C25A H25A 114.9 . . ?
N1A C26A H26A 109.5 . . ?
N1A C26A H26B 109.5 . . ?
N1A C26A H26C 109.5 . . ?
H26A C26A H26B 109.5 . . ?
H26A C26A H26C 109.5 . . ?
H26B C26A H26C 109.5 . . ?
N1A C27A H27A 109.5 . . ?
N1A C27A H27B 109.5 . . ?
N1A C27A H27C 109.5 . . ?
H27A C27A H27B 109.5 . . ?
H27A C27A H27C 109.5 . . ?
H27B C27A H27C 109.5 . . ?
C25B N1B C26B 110.1(18) . . ?
C25B N1B C27B 118.8(18) . . ?
C26B N1B C27B 131(2) . . ?
O3 C25B N1B 134(2) . . ?
O3 C25B H25B 113.1 . . ?
N1B C25B H25B 113.1 . . ?
N1B C26B H26D 109.5 . . ?
N1B C26B H26E 109.5 . . ?
N1B C26B H26F 109.5 . . ?
H26D C26B H26E 109.5 . . ?
H26D C26B H26F 109.5 . . ?
H26E C26B H26F 109.5 . . ?
N1B C27B H27D 109.5 . . ?
N1B C27B H27E 109.5 . . ?
N1B C27B H27F 109.5 . . ?
H27D C27B H27E 109.5 . . ?
H27D C27B H27F 109.5 . . ?
H27E C27B H27F 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
O1 H1 0.8400 . ?
O1 C17 1.4437(19) . ?
O2 H2 0.8400 . ?
O2 C22 1.438(2) . ?
C1 C2 1.407(2) . ?
C1 C14 1.403(2) . ?
C1 C15 1.435(2) . ?
C2 C3 1.515(2) . ?
C2 C11 1.394(2) . ?
C3 H3 1.01(2) . ?
C3 C4 1.514(2) . ?
C3 C10 1.613(2) 2_656 ?
C4 C5 1.386(3) . ?
C4 C9 1.398(2) . ?
C5 H5 1.00(2) . ?
C5 C6 1.399(2) . ?
C6 H6 0.95(3) . ?
C6 C7 1.380(3) . ?
C7 H7 0.91(3) . ?
C7 C8 1.405(3) . ?
C8 C9 1.408(2) . ?
C8 C20 1.433(2) . ?
C9 C10 1.510(2) . ?
C10 H10 0.99(2) . ?
C10 C11 1.514(2) . ?
C11 C12 1.390(2) . ?
C12 H12 1.02(2) . ?
C12 C13 1.397(2) . ?
C13 H13 1.00(2) . ?
C13 C14 1.380(3) . ?
C14 H14 1.00(2) . ?
C15 C16 1.202(3) . ?
C16 C17 1.475(3) . ?
C17 C18 1.524(3) . ?
C17 C19 1.528(2) . ?
C18 H18A 0.98(3) . ?
C18 H18B 1.01(3) . ?
C18 H18C 0.98(3) . ?
C19 H19A 1.04(3) . ?
C19 H19B 0.97(3) . ?
C19 H19C 1.04(3) . ?
C20 C21 1.202(3) . ?
C21 C22 1.478(2) . ?
C22 C23 1.524(2) . ?
C22 C24 1.527(2) . ?
C23 H23A 1.02(3) . ?
C23 H23B 1.02(3) . ?
C23 H23C 1.00(3) . ?
C24 H24A 0.98(3) . ?
C24 H24B 1.04(3) . ?
C24 H24C 0.96(3) . ?
O3 C25A 1.166(9) . ?
O3 C25B 1.23(2) . ?
N1A C25A 1.397(14) . ?
N1A C26A 1.439(15) . ?
N1A C27A 1.413(15) . ?
C25A H25A 0.9500 . ?
C26A H26A 0.9800 . ?
C26A H26B 0.9800 . ?
C26A H26C 0.9800 . ?
C27A H27A 0.9800 . ?
C27A H27B 0.9800 . ?
C27A H27C 0.9800 . ?
N1B C25B 1.30(2) . ?
N1B C26B 1.382(18) . ?
N1B C27B 1.400(19) . ?
C25B H25B 0.9500 . ?
C26B H26D 0.9800 . ?
C26B H26E 0.9800 . ?
C26B H26F 0.9800 . ?
C27B H27D 0.9800 . ?
C27B H27E 0.9800 . ?
C27B H27F 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
C1 C2 C3 C4 134.22(17) . . . . ?
C1 C2 C3 C10 -102.54(19) . . . 2_656 ?
C1 C2 C11 C10 -179.05(16) . . . . ?
C1 C2 C11 C12 1.4(3) . . . . ?
C2 C1 C14 C13 0.9(3) . . . . ?
C2 C3 C4 C5 -134.42(16) . . . . ?
C2 C3 C4 C9 45.03(19) . . . . ?
C2 C11 C12 C13 0.2(3) . . . . ?
C3 C2 C11 C10 0.8(2) . . . . ?
C3 C2 C11 C12 -178.79(16) . . . . ?
C3 C4 C5 C6 179.77(15) . . . . ?
C3 C4 C9 C8 -178.64(14) . . . . ?
C3 C4 C9 C10 0.3(2) . . . . ?
C3 C10 C11 C2 -78.84(19) 2_656 . . . ?
C3 C10 C11 C12 100.71(18) 2_656 . . . ?
C4 C5 C6 C7 -0.7(2) . . . . ?
C4 C9 C10 C3 77.85(17) . . . 2_656 ?
C4 C9 C10 C11 -45.16(18) . . . . ?
C5 C4 C9 C8 0.8(2) . . . . ?
C5 C4 C9 C10 179.73(14) . . . . ?
C5 C6 C7 C8 -0.2(3) . . . . ?
C6 C7 C8 C9 1.3(2) . . . . ?
C6 C7 C8 C20 -175.73(16) . . . . ?
C7 C8 C9 C4 -1.6(2) . . . . ?
C7 C8 C9 C10 179.52(15) . . . . ?
C8 C9 C10 C3 -103.29(17) . . . 2_656 ?
C8 C9 C10 C11 133.70(16) . . . . ?
C9 C4 C5 C6 0.3(2) . . . . ?
C9 C10 C11 C2 44.6(2) . . . . ?
C9 C10 C11 C12 -135.82(17) . . . . ?
C10 C3 C4 C5 102.52(18) 2_656 . . . ?
C10 C3 C4 C9 -78.04(17) 2_656 . . . ?
C10 C11 C12 C13 -179.35(18) . . . . ?
C11 C2 C3 C4 -45.6(2) . . . . ?
C11 C2 C3 C10 77.66(18) . . . 2_656 ?
C11 C12 C13 C14 -1.2(3) . . . . ?
C12 C13 C14 C1 0.6(3) . . . . ?
C14 C1 C2 C3 178.25(17) . . . . ?
C14 C1 C2 C11 -2.0(3) . . . . ?
C15 C1 C2 C3 -4.0(3) . . . . ?
C15 C1 C2 C11 175.81(16) . . . . ?
C15 C1 C14 C13 -176.77(18) . . . . ?
C20 C8 C9 C4 175.45(15) . . . . ?
C20 C8 C9 C10 -3.4(2) . . . . ?
C26A N1A C25A O3 -8.2(14) . . . . ?
C27A N1A C25A O3 177.4(14) . . . . ?
C26B N1B C25B O3 -4(3) . . . . ?
C27B N1B C25B O3 174(2) . . . . ?
loop_
_twin_individual_id
_twin_individual_mass_fraction_refined
_oxdiff_twin_reflns_isolated
_oxdiff_twin_reflns_overlapped
_twin_individual_twin_lattice_type
_twin_individual_twin_matrix_11
_twin_individual_twin_matrix_12
_twin_individual_twin_matrix_13
_twin_individual_twin_matrix_21
_twin_individual_twin_matrix_22
_twin_individual_twin_matrix_23
_twin_individual_twin_matrix_31
_twin_individual_twin_matrix_32
_twin_individual_twin_matrix_33
1 0.6396(14) 4509 4258 ref 1.0000 0.0000 0.0000 0.0000 1.0000 0.0000 0.0000
0.0000 1.0000
2 0.3604(14) 4536 4258 nmt 1.0152 0.0183 0.0358 -0.0208 0.9877 -0.0332 -0.0364
0.0136 0.9946
loop_
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
0.0023 0.9971 -0.0006 -0.0052 -0.0595 -0.1451
-0.0023 -0.9971 0.0006 0.0052 0.0595 0.1451
0.0009 -0.0009 -1.0007 -0.1410 -0.0011 0.0274
-0.0009 0.0009 1.0007 0.1410 0.0011 -0.0274
2.0054 -1.0025 -0.9995 -0.0461 -0.2842 0.1457
-2.0054 1.0025 0.9995 0.0461 0.2842 -0.1457
