#------------------------------------------------------------------------------
#$Date: 2020-12-19 03:56:35 +0200 (Sat, 19 Dec 2020) $
#$Revision: 259977 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/12/76/7127653.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_7127653
loop_
_publ_author_name
'Göbel, Dominik'
'Rusch, Pascal'
'Duvinage, Daniel'
'Bigall, Nadja C.'
'Nachtsheim, Boris J.'
_publ_section_title
;
 Emission color-tunable oxazol(in)yl-substituted excited-state
 intramolecular proton transfer (ESIPT)-based luminophores.
;
_journal_issue                   98
_journal_name_full
'Chemical communications (Cambridge, England)'
_journal_page_first              15430
_journal_page_last               15433
_journal_paper_doi               10.1039/d0cc05780k
_journal_volume                  56
_journal_year                    2020
_chemical_formula_moiety         'C25 H28 N2 O4, C6 H12'
_chemical_formula_sum            'C31 H40 N2 O4'
_chemical_formula_weight         504.65
_space_group_crystal_system      orthorhombic
_space_group_IT_number           56
_space_group_name_Hall           '-P 2ab 2ac'
_space_group_name_H-M_alt        'P c c n'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_audit_creation_date             2020-06-21
_audit_creation_method
;
Olex2 1.3-dev
(compiled 2020.03.26 svn.re84ffbc8 for OlexSys, GUI svn.r6014)
;
_audit_update_record
;
2020-07-21 deposited with the CCDC.	2020-11-10 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   20.5800(6)
_cell_length_b                   24.0995(7)
_cell_length_c                   11.4414(3)
_cell_measurement_reflns_used    9918
_cell_measurement_temperature    100.0
_cell_measurement_theta_max      30.50
_cell_measurement_theta_min      2.65
_cell_volume                     5674.6(3)
_computing_molecular_graphics    'Olex2 1.3-dev (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3-dev (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2016/4 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      100.0
_diffrn_detector                 'Bruker PHOTON area detector'
_diffrn_detector_area_resol_mean 7.9
_diffrn_detector_type            'CMOS area detector'
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  'Bruker D8 Venture PHOTON area detector'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_radiation_monochromator  'mirror optics'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0434
_diffrn_reflns_av_unetI/netI     0.0258
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       27
_diffrn_reflns_limit_h_min       -25
_diffrn_reflns_limit_k_max       29
_diffrn_reflns_limit_k_min       -32
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            61897
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.280
_diffrn_reflns_theta_min         2.205
_diffrn_source                   'microfocus sealed X-ray tube'
_diffrn_source_type              'Incoatec I\ms'
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.078
_exptl_absorpt_correction_T_max  0.7461
_exptl_absorpt_correction_T_min  0.7080
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0924 before and 0.0584 after correction.
The Ratio of minimum to maximum transmission is 0.9489.
The λ/2 correction factor is Not present.
;
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.181
_exptl_crystal_description       prism
_exptl_crystal_F_000             2176
_exptl_crystal_size_max          0.5
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.3
_refine_diff_density_max         0.319
_refine_diff_density_min         -0.215
_refine_diff_density_rms         0.043
_refine_ls_extinction_coef       0.0048(5)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2016/4 (Sheldrick 2016)'
_refine_ls_goodness_of_fit_ref   1.029
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     404
_refine_ls_number_reflns         7040
_refine_ls_number_restraints     36
_refine_ls_restrained_S_all      1.032
_refine_ls_R_factor_all          0.0592
_refine_ls_R_factor_gt           0.0425
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0412P)²+2.8482P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0960
_refine_ls_wR_factor_ref         0.1052
_reflns_Friedel_coverage         0.000
_reflns_number_gt                5628
_reflns_number_total             7040
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d0cc05780k2.cif
_cod_data_source_block           goebeld180425_0ma
_cod_database_code               7127653
_shelx_shelxl_version_number     2016/4
_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   0.977
_shelx_estimated_absorpt_t_min   0.962
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Uiso/Uaniso restraints and constraints
Uanis(C40) \\sim Ueq, Uanis(C41) \\sim Ueq, Uanis(C42) \\sim Ueq, Uanis(C43)
\\sim Ueq, Uanis(C44) \\sim Ueq, Uanis(C45) \\sim Ueq: with sigma of 0.008 and
sigma for terminal atoms of 0.014
3. Others
 Sof(C40)=Sof(H40A)=Sof(H40B)=Sof(C41)=Sof(H41A)=Sof(H41B)=Sof(C42)=Sof(H42A)=
 Sof(H42B)=Sof(C43)=Sof(H43A)=Sof(H43B)=Sof(C44)=Sof(H44A)=Sof(H44B)=Sof(C45)=
 Sof(H45A)=Sof(H45B)=1-FVAR(1)
 Sof(C30)=Sof(H30A)=Sof(H30B)=Sof(C31)=Sof(H31A)=Sof(H31B)=Sof(C32)=Sof(H32A)=
 Sof(H32B)=Sof(C33)=Sof(H33A)=Sof(H33B)=Sof(C34)=Sof(H34A)=Sof(H34B)=Sof(C35)=
 Sof(H35A)=Sof(H35B)=FVAR(1)
4.a Secondary CH2 refined with riding coordinates:
 C13(H13A,H13B), C18(H18A,H18B), C30(H30A,H30B), C31(H31A,H31B), C32(H32A,
 H32B), C33(H33A,H33B), C34(H34A,H34B), C35(H35A,H35B), C40(H40A,H40B),
 C41(H41A,H41B), C42(H42A,H42B), C43(H43A,H43B), C44(H44A,H44B), C45(H45A,H45B)
4.b Aromatic/amide H refined with riding coordinates:
 C1(H1A), C4(H4), C5(H5), C8(H8)
4.c Idealised Me refined as rotating group:
 C10(H10A,H10B,H10C), C11(H11A,H11B,H11C), C15(H15A,H15B,H15C), C16(H16A,H16B,
 H16C), C20(H20A,H20B,H20C), C21(H21A,H21B,H21C)
;
_olex2_submission_special_instructions 'No special instructions were received'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y+1/2, z'
'-x, y+1/2, -z+1/2'
'x+1/2, -y, -z+1/2'
'-x, -y, -z'
'x-1/2, y-1/2, -z'
'x, -y-1/2, z-1/2'
'-x-1/2, y, z-1/2'
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
O2 O 0.77605(4) 0.47394(4) 0.40795(8) 0.0219(2) Uani 1 1 d . . . . .
O1 O 0.59627(4) 0.54879(3) 0.47297(8) 0.01892(19) Uani 1 1 d . . . . .
O4 O 0.48963(4) 0.22070(3) 0.96044(8) 0.01993(19) Uani 1 1 d . . . . .
O3 O 0.39557(4) 0.37156(4) 0.89664(8) 0.02006(19) Uani 1 1 d . . . . .
N1 N 0.71046(5) 0.54771(4) 0.37887(8) 0.0167(2) Uani 1 1 d . . . . .
N2 N 0.40084(5) 0.27378(4) 0.99080(9) 0.0172(2) Uani 1 1 d . . . . .
C1 C 0.68409(6) 0.42037(5) 0.55013(10) 0.0167(2) Uani 1 1 d . . . . .
H1A H 0.723938 0.401997 0.534027 0.020 Uiso 1 1 calc R U . . .
C2 C 0.67062(5) 0.47199(5) 0.49860(10) 0.0153(2) Uani 1 1 d . . . . .
C3 C 0.61103(5) 0.49911(5) 0.52125(10) 0.0152(2) Uani 1 1 d . . . . .
C4B C 0.54291(5) 0.39112(5) 0.73018(10) 0.0147(2) Uani 1 1 d . . . . .
C4A C 0.58068(5) 0.42449(5) 0.64747(10) 0.0148(2) Uani 1 1 d . . . . .
C4 C 0.56589(5) 0.47511(5) 0.59649(10) 0.0156(2) Uani 1 1 d . . . . .
H4 H 0.525775 0.493063 0.612550 0.019 Uiso 1 1 calc R U . . .
C5 C 0.48236(6) 0.40138(5) 0.77820(10) 0.0155(2) Uani 1 1 d . . . . .
H5 H 0.459875 0.434878 0.761482 0.019 Uiso 1 1 calc R U . . .
C6 C 0.45509(5) 0.36156(5) 0.85154(10) 0.0158(2) Uani 1 1 d . . . . .
C7 C 0.48918(6) 0.31177(5) 0.87499(10) 0.0155(2) Uani 1 1 d . . . . .
C8 C 0.55101(5) 0.30281(5) 0.82682(10) 0.0165(2) Uani 1 1 d . . . . .
H8 H 0.574197 0.269733 0.844134 0.020 Uiso 1 1 calc R U . . .
C8A C 0.57786(5) 0.34220(5) 0.75437(10) 0.0159(2) Uani 1 1 d . . . . .
C9 C 0.64249(5) 0.34119(5) 0.68916(10) 0.0174(2) Uani 1 1 d . . . . .
C9A C 0.63929(5) 0.39645(5) 0.62416(10) 0.0162(2) Uani 1 1 d . . . . .
C10 C 0.70009(6) 0.33862(6) 0.77439(13) 0.0258(3) Uani 1 1 d . . . . .
H10A H 0.740895 0.340273 0.730364 0.039 Uiso 1 1 calc R U . . .
H10B H 0.698275 0.303850 0.818688 0.039 Uiso 1 1 calc R U . . .
H10C H 0.697857 0.370092 0.828479 0.039 Uiso 1 1 calc R U . . .
C11 C 0.64591(6) 0.29243(5) 0.60268(12) 0.0245(3) Uani 1 1 d . . . . .
H11A H 0.608918 0.294305 0.548886 0.037 Uiso 1 1 calc R U . . .
H11B H 0.644483 0.257345 0.645897 0.037 Uiso 1 1 calc R U . . .
H11C H 0.686508 0.294576 0.558145 0.037 Uiso 1 1 calc R U . . .
C12 C 0.71855(5) 0.49989(5) 0.42547(10) 0.0156(2) Uani 1 1 d . . . . .
C13 C 0.81565(6) 0.51290(6) 0.34221(13) 0.0300(3) Uani 1 1 d . . . . .
H13A H 0.832585 0.495377 0.270124 0.036 Uiso 1 1 calc R U . . .
H13B H 0.852806 0.525922 0.389846 0.036 Uiso 1 1 calc R U . . .
C14 C 0.76991(5) 0.56161(5) 0.31208(10) 0.0173(2) Uani 1 1 d . . . . .
C15 C 0.75273(7) 0.56368(6) 0.18293(10) 0.0255(3) Uani 1 1 d . . . . .
H15A H 0.735239 0.527680 0.158517 0.038 Uiso 1 1 calc R U . . .
H15B H 0.791821 0.572108 0.137336 0.038 Uiso 1 1 calc R U . . .
H15C H 0.720069 0.592594 0.169665 0.038 Uiso 1 1 calc R U . . .
C16 C 0.79698(6) 0.61697(6) 0.35294(12) 0.0270(3) Uani 1 1 d . . . . .
H16A H 0.766318 0.646633 0.333138 0.041 Uiso 1 1 calc R U . . .
H16B H 0.838658 0.623983 0.314248 0.041 Uiso 1 1 calc R U . . .
H16C H 0.803406 0.615999 0.437783 0.041 Uiso 1 1 calc R U . . .
C17 C 0.45744(6) 0.26930(5) 0.94561(10) 0.0158(2) Uani 1 1 d . . . . .
C18 C 0.45031(6) 0.18948(5) 1.04373(11) 0.0210(3) Uani 1 1 d . . . . .
H18A H 0.470140 0.190284 1.122543 0.025 Uiso 1 1 calc R U . . .
H18B H 0.445551 0.150377 1.018603 0.025 Uiso 1 1 calc R U . . .
C19 C 0.38412(6) 0.21926(5) 1.04365(10) 0.0175(2) Uani 1 1 d . . . . .
C20 C 0.33519(6) 0.19028(5) 0.96464(11) 0.0248(3) Uani 1 1 d . . . . .
H20A H 0.296278 0.213425 0.956845 0.037 Uiso 1 1 calc R U . . .
H20B H 0.323243 0.154419 0.998846 0.037 Uiso 1 1 calc R U . . .
H20C H 0.354555 0.184339 0.887399 0.037 Uiso 1 1 calc R U . . .
C21 C 0.35740(6) 0.22727(5) 1.16624(11) 0.0239(3) Uani 1 1 d . . . . .
H21A H 0.388463 0.248731 1.212840 0.036 Uiso 1 1 calc R U . . .
H21B H 0.350493 0.190977 1.202804 0.036 Uiso 1 1 calc R U . . .
H21C H 0.316006 0.247279 1.162156 0.036 Uiso 1 1 calc R U . . .
C30 C 0.40822(12) 0.54242(8) 0.8190(2) 0.0332(5) Uani 0.794(4) 1 d . . P A 1
H30A H 0.420196 0.526792 0.741931 0.040 Uiso 0.794(4) 1 calc R U P A 1
H30B H 0.384657 0.513420 0.863257 0.040 Uiso 0.794(4) 1 calc R U P A 1
C31 C 0.46976(15) 0.55844(9) 0.8852(2) 0.0368(6) Uani 0.794(4) 1 d . . P A 1
H31A H 0.458181 0.569366 0.965920 0.044 Uiso 0.794(4) 1 calc R U P A 1
H31B H 0.499030 0.525912 0.889657 0.044 Uiso 0.794(4) 1 calc R U P A 1
C32 C 0.50507(11) 0.60609(11) 0.8259(3) 0.0331(6) Uani 0.794(4) 1 d . . P A 1
H32A H 0.522150 0.593421 0.749521 0.040 Uiso 0.794(4) 1 calc R U P A 1
H32B H 0.542436 0.617558 0.874723 0.040 Uiso 0.794(4) 1 calc R U P A 1
C33 C 0.46026(10) 0.65577(8) 0.80688(17) 0.0318(5) Uani 0.794(4) 1 d . . P A 1
H33A H 0.447473 0.671370 0.883548 0.038 Uiso 0.794(4) 1 calc R U P A 1
H33B H 0.483844 0.684911 0.763082 0.038 Uiso 0.794(4) 1 calc R U P A 1
C34 C 0.39961(11) 0.63910(9) 0.73932(19) 0.0317(5) Uani 0.794(4) 1 d . . P A 1
H34A H 0.370430 0.671554 0.731704 0.038 Uiso 0.794(4) 1 calc R U P A 1
H34B H 0.412024 0.626905 0.659768 0.038 Uiso 0.794(4) 1 calc R U P A 1
C35 C 0.36389(12) 0.59230(11) 0.8014(3) 0.0304(6) Uani 0.794(4) 1 d . . P A 1
H35A H 0.325650 0.581100 0.754456 0.037 Uiso 0.794(4) 1 calc R U P A 1
H35B H 0.348162 0.605554 0.878228 0.037 Uiso 0.794(4) 1 calc R U P A 1
C40 C 0.3784(5) 0.6106(5) 0.7686(9) 0.033(2) Uani 0.206(4) 1 d . U P A 2
H40A H 0.371124 0.644280 0.816286 0.040 Uiso 0.206(4) 1 calc R U P A 2
H40B H 0.341436 0.606769 0.713779 0.040 Uiso 0.206(4) 1 calc R U P A 2
C41 C 0.3810(5) 0.5607(5) 0.8471(9) 0.046(2) Uani 0.206(4) 1 d . U P A 2
H41A H 0.386295 0.526749 0.799392 0.055 Uiso 0.206(4) 1 calc R U P A 2
H41B H 0.339697 0.557539 0.891053 0.055 Uiso 0.206(4) 1 calc R U P A 2
C42 C 0.4377(6) 0.5658(5) 0.9328(9) 0.054(3) Uani 0.206(4) 1 d . U P A 2
H42A H 0.429991 0.597324 0.986508 0.065 Uiso 0.206(4) 1 calc R U P A 2
H42B H 0.441040 0.531512 0.980140 0.065 Uiso 0.206(4) 1 calc R U P A 2
C43 C 0.5007(5) 0.5750(6) 0.8655(9) 0.042(2) Uani 0.206(4) 1 d . U P A 2
H43A H 0.536523 0.581790 0.921569 0.050 Uiso 0.206(4) 1 calc R U P A 2
H43B H 0.511396 0.541051 0.820659 0.050 Uiso 0.206(4) 1 calc R U P A 2
C44 C 0.4957(6) 0.6223(7) 0.7849(12) 0.060(4) Uani 0.206(4) 1 d . U P A 2
H44A H 0.536877 0.625760 0.740756 0.072 Uiso 0.206(4) 1 calc R U P A 2
H44B H 0.489811 0.656723 0.830866 0.072 Uiso 0.206(4) 1 calc R U P A 2
C45 C 0.4406(5) 0.6169(5) 0.7000(9) 0.056(3) Uani 0.206(4) 1 d . U P A 2
H45A H 0.447356 0.584156 0.649232 0.067 Uiso 0.206(4) 1 calc R U P A 2
H45B H 0.438267 0.650337 0.649765 0.067 Uiso 0.206(4) 1 calc R U P A 2
H3 H 0.3843(9) 0.3400(8) 0.9410(17) 0.052(5) Uiso 1 1 d . . . . .
H1 H 0.6315(10) 0.5599(8) 0.4301(17) 0.054(6) 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 0.0033 0.0016 '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 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 '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
C12 O2 C13 105.58(9) . . ?
C32a C31a C30 111.54(18) . . ?
C3 O1 H1 107.4(12) . . ?
C17 O4 C18 104.85(9) . . ?
C6 O3 H3 106.5(12) . . ?
C34a C35a C30 110.9(2) . . ?
C35a C30a H30A 109.4 . . ?
C12 N1 C14 108.13(10) . . ?
C17 N2 C19 107.50(9) . . ?
C2 C1 H1A 120.1 . . ?
C9A C1 H1A 120.1 . . ?
C9A C1 C2 119.76(11) . . ?
C1 C2 C3 120.26(10) . . ?
C1 C2 C12 121.06(10) . . ?
C31a C30a H30A 109.4 . . ?
C35a C30a H30B 109.4 . . ?
C31a C30a H30B 109.4 . . ?
H30Aa C30a H30B 108.0 . . ?
C35a C30a C31 111.32(17) . . ?
C32a C31a H31A 109.3 . . ?
C30a C31a H31A 109.3 . . ?
H31Aa C31a H31B 108.0 . . ?
C30a C31a H31B 109.3 . . ?
C32a C31a H31B 109.3 . . ?
C34a C33a C32 111.14(17) . . ?
C31a C32a H32A 109.3 . . ?
C33a C32a H32A 109.3 . . ?
H32Aa C32a H32B 108.0 . . ?
C33a C32a H32B 109.3 . . ?
C3 C2 C12 118.61(10) . . ?
O1 C3 C2 121.94(10) . . ?
O1 C3 C4 118.05(10) . . ?
C4 C3 C2 120.00(10) . . ?
C5 C4B C4A 129.50(10) . . ?
C5 C4B C8A 122.09(10) . . ?
C8A C4B C4A 108.39(10) . . ?
C4 C4A C4B 129.68(11) . . ?
C4 C4A C9A 122.06(10) . . ?
C9A C4A C4B 108.26(10) . . ?
C3 C4 H4 120.7 . . ?
C31a C32a H32B 109.3 . . ?
C35a C34a C33 110.78(18) . . ?
C31a C32a C33 111.56(19) . . ?
C32a C33a H33A 109.4 . . ?
C34a C33a H33A 109.4 . . ?
C32a C33a H33B 109.4 . . ?
C34a C33a H33B 109.4 . . ?
H33Aa C33a H33B 108.0 . . ?
C35a C34a H34A 109.5 . . ?
C33a C34a H34A 109.5 . . ?
C35a C34a H34B 109.5 . . ?
H34Aa C34a H34B 108.1 . . ?
C33a C34a H34B 109.5 . . ?
C34a C35a H35A 109.5 . . ?
C30a C35a H35A 109.5 . . ?
C34a C35a H35B 109.5 . . ?
H35Aa C35a H35B 108.0 . . ?
C30a C35a H35B 109.5 . . ?
C44b C45b C40 108.3(9) . . ?
C41b C40b H40A 109.4 . . ?
C45b C40b H40A 109.4 . . ?
H40Ab C40b H40B 108.0 . . ?
C45b C40b H40B 109.4 . . ?
C41b C40b H40B 109.4 . . ?
C4A C4 C3 118.64(10) . . ?
C4A C4 H4 120.7 . . ?
C4B C5 H5 120.7 . . ?
C4B C5 C6 118.62(10) . . ?
C6 C5 H5 120.7 . . ?
O3 C6 C5 118.20(10) . . ?
O3 C6 C7 121.89(10) . . ?
C5 C6 C7 119.90(10) . . ?
C6 C7 C17 118.55(10) . . ?
C8 C7 C6 120.36(10) . . ?
C8 C7 C17 121.04(10) . . ?
C7 C8 H8 120.2 . . ?
C8A C8 C7 119.64(10) . . ?
C8A C8 H8 120.2 . . ?
C4B C8A C9 111.25(10) . . ?
C8 C8A C4B 119.39(10) . . ?
C8 C8A C9 129.34(10) . . ?
C8A C9 C9A 100.76(9) . . ?
C8A C9 C10 111.29(10) . . ?
C8A C9 C11 111.52(10) . . ?
C9A C9 C10 112.19(10) . . ?
C9A C9 C11 110.79(10) . . ?
C10 C9 C11 110.01(10) . . ?
C1 C9A C4A 119.25(10) . . ?
C1 C9A C9 129.44(10) . . ?
C4A C9A C9 111.31(10) . . ?
C9 C10 H10A 109.5 . . ?
C9 C10 H10B 109.5 . . ?
C9 C10 H10C 109.5 . . ?
H10A C10 H10B 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C9 C11 H11A 109.5 . . ?
C9 C11 H11B 109.5 . . ?
C9 C11 H11C 109.5 . . ?
H11A C11 H11B 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
O2 C12 C2 117.61(10) . . ?
N1 C12 O2 117.89(10) . . ?
N1 C12 C2 124.48(11) . . ?
O2 C13 H13A 110.7 . . ?
O2 C13 H13B 110.7 . . ?
O2 C13 C14 105.36(10) . . ?
H13A C13 H13B 108.8 . . ?
C14 C13 H13A 110.7 . . ?
C14 C13 H13B 110.7 . . ?
N1 C14 C13 102.50(9) . . ?
N1 C14 C15 108.48(10) . . ?
N1 C14 C16 110.04(10) . . ?
C15 C14 C13 112.58(11) . . ?
C16 C14 C13 112.05(11) . . ?
C16 C14 C15 110.82(10) . . ?
C14 C15 H15A 109.5 . . ?
C14 C15 H15B 109.5 . . ?
C14 C15 H15C 109.5 . . ?
H15A C15 H15B 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C14 C16 H16A 109.5 . . ?
C14 C16 H16B 109.5 . . ?
C14 C16 H16C 109.5 . . ?
H16A C16 H16B 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
O4 C17 C7 117.17(10) . . ?
N2 C17 O4 117.84(10) . . ?
N2 C17 C7 124.94(10) . . ?
O4 C18 H18A 110.9 . . ?
O4 C18 H18B 110.9 . . ?
O4 C18 C19 104.47(9) . . ?
H18A C18 H18B 108.9 . . ?
C19 C18 H18A 110.9 . . ?
C19 C18 H18B 110.9 . . ?
N2 C19 C18 101.98(9) . . ?
N2 C19 C20 108.48(10) . . ?
N2 C19 C21 110.31(10) . . ?
C20 C19 C18 111.81(10) . . ?
C21 C19 C18 112.27(10) . . ?
C21 C19 C20 111.53(10) . . ?
C19 C20 H20A 109.5 . . ?
C19 C20 H20B 109.5 . . ?
C19 C20 H20C 109.5 . . ?
H20A C20 H20B 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
C19 C21 H21A 109.5 . . ?
C19 C21 H21B 109.5 . . ?
C19 C21 H21C 109.5 . . ?
H21A C21 H21B 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
C43b C42b C41 109.7(8) . . ?
C42b C41b H41A 109.6 . . ?
C40b C41b H41A 109.6 . . ?
C40b C41b H41B 109.6 . . ?
H41Ab C41b H41B 108.1 . . ?
C42b C41b H41B 109.6 . . ?
C44b C43b C42 111.7(10) . . ?
C40b C41b C42 110.3(8) . . ?
C41b C42b H42A 109.7 . . ?
C43b C42b H42A 109.7 . . ?
H42Ab C42b H42B 108.2 . . ?
C43b C42b H42B 109.7 . . ?
C41b C42b H42B 109.7 . . ?
C42b C43b H43A 109.3 . . ?
C44b C43b H43A 109.3 . . ?
C44b C43b H43B 109.3 . . ?
C42b C43b H43B 109.3 . . ?
H43Ab C43b H43B 107.9 . . ?
C45b C44b H44A 108.9 . . ?
C43b C44b H44A 108.9 . . ?
C45b C44b H44B 108.9 . . ?
H44Ab C44b H44B 107.8 . . ?
C43b C44b H44B 108.9 . . ?
C41b C40b C45 111.3(8) . . ?
C43b C44b C45 113.2(10) . . ?
C40b C45b H45A 110.0 . . ?
C44b C45b H45A 110.0 . . ?
C40b C45b H45B 110.0 . . ?
C44b C45b H45B 110.0 . . ?
H45Ab C45b H45B 108.4 . . ?
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
O2 C12 1.3534(14) . ?
O2 C13 1.4531(15) . ?
C30a H30A 0.9900 . ?
C30a H30B 0.9900 . ?
C30a C31 1.525(3) . ?
C31a H31A 0.9900 . ?
C31a H31B 0.9900 . ?
C31a C32 1.519(4) . ?
C32a H32A 0.9900 . ?
C32a H32B 0.9900 . ?
C32a C33 1.527(3) . ?
C33a H33A 0.9900 . ?
C33a H33B 0.9900 . ?
C33a C34 1.522(3) . ?
C34a H34A 0.9900 . ?
C34a H34B 0.9900 . ?
C30a C35 1.522(3) . ?
C34a C35 1.522(3) . ?
C35a H35A 0.9900 . ?
C35a H35B 0.9900 . ?
C40b H40A 0.9900 . ?
C40b H40B 0.9900 . ?
C40b C41 1.502(14) . ?
C41b H41A 0.9900 . ?
C41b H41B 0.9900 . ?
C41b C42 1.529(14) . ?
C42b H42A 0.9900 . ?
C42b H42B 0.9900 . ?
C42b C43 1.525(14) . ?
C43b H43A 0.9900 . ?
C43b H43B 0.9900 . ?
C43b C44 1.471(15) . ?
C44b H44A 0.9900 . ?
C44b H44B 0.9900 . ?
C40b C45 1.510(14) . ?
C44b C45 1.498(14) . ?
C45b H45A 0.9900 . ?
C45b H45B 0.9900 . ?
O1 C3 1.3530(14) . ?
O1 H1 0.92(2) . ?
O4 C17 1.3562(14) . ?
O4 C18 1.4592(14) . ?
O3 C6 1.3509(14) . ?
O3 H3 0.94(2) . ?
N1 C12 1.2806(15) . ?
N1 C14 1.4809(14) . ?
N2 C17 1.2791(15) . ?
N2 C19 1.4866(14) . ?
C1 H1A 0.9500 . ?
C1 C2 1.4043(16) . ?
C1 C9A 1.3783(16) . ?
C2 C3 1.4137(16) . ?
C2 C12 1.4579(16) . ?
C3 C4 1.3923(16) . ?
C4B C4A 1.4650(15) . ?
C4B C5 1.3841(16) . ?
C4B C8A 1.4085(16) . ?
C4A C4 1.3860(16) . ?
C4A C9A 1.4081(16) . ?
C4 H4 0.9500 . ?
C5 H5 0.9500 . ?
C5 C6 1.3928(16) . ?
C6 C7 1.4156(16) . ?
C7 C8 1.4034(16) . ?
C7 C17 1.4584(15) . ?
C8 H8 0.9500 . ?
C8 C8A 1.3761(16) . ?
C8A C9 1.5251(16) . ?
C9 C9A 1.5266(16) . ?
C9 C10 1.5363(17) . ?
C9 C11 1.5378(17) . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 0.9800 . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 0.9800 . ?
C13 H13A 0.9900 . ?
C13 H13B 0.9900 . ?
C13 C14 1.5437(17) . ?
C14 C15 1.5202(16) . ?
C14 C16 1.5195(17) . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C15 H15C 0.9800 . ?
C16 H16A 0.9800 . ?
C16 H16B 0.9800 . ?
C16 H16C 0.9800 . ?
C18 H18A 0.9900 . ?
C18 H18B 0.9900 . ?
C18 C19 1.5396(17) . ?
C19 C20 1.5229(17) . ?
C19 C21 1.5189(17) . ?
C20 H20A 0.9800 . ?
C20 H20B 0.9800 . ?
C20 H20C 0.9800 . ?
C21 H21A 0.9800 . ?
C21 H21B 0.9800 . ?
C21 H21C 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
C40b C41b C42b C43b -55.1(13) . . . . ?
C31a C32a C33a C34a -55.0(3) . . . . ?
C35a C30a C31a C32a -54.5(3) . . . . ?
C41b C40b C45b C44b -58.7(13) . . . . ?
C33a C34a C35a C30a -56.9(3) . . . . ?
C45b C40b C41b C42b 59.2(12) . . . . ?
C30a C31a C32a C33a 54.0(3) . . . . ?
C43b C44b C45b C40b 57.6(16) . . . . ?
C32a C33a C34a C35a 56.3(3) . . . . ?
C41b C42b C43b C44b 53.6(13) . . . . ?
C31a C30a C35a C34a 56.0(3) . . . . ?
C42b C43b C44b C45b -56.3(15) . . . . ?
O2 C13 C14 N1 7.19(13) . . . . ?
O2 C13 C14 C15 -109.16(12) . . . . ?
O2 C13 C14 C16 125.13(11) . . . . ?
O1 C3 C4 C4A -179.35(10) . . . . ?
O4 C18 C19 N2 -17.86(12) . . . . ?
O4 C18 C19 C20 97.85(11) . . . . ?
O4 C18 C19 C21 -135.91(10) . . . . ?
O3 C6 C7 C8 -179.88(10) . . . . ?
O3 C6 C7 C17 2.82(16) . . . . ?
C1 C2 C3 O1 -179.83(10) . . . . ?
C1 C2 C3 C4 1.12(17) . . . . ?
C1 C2 C12 O2 0.80(16) . . . . ?
C1 C2 C12 N1 -177.63(11) . . . . ?
C2 C1 C9A C4A -0.39(17) . . . . ?
C2 C1 C9A C9 179.49(11) . . . . ?
C2 C3 C4 C4A -0.26(16) . . . . ?
C3 C2 C12 O2 177.96(10) . . . . ?
C3 C2 C12 N1 -0.46(17) . . . . ?
C4B C4A C4 C3 178.85(11) . . . . ?
C4B C4A C9A C1 -178.55(10) . . . . ?
C4B C4A C9A C9 1.55(13) . . . . ?
C4B C5 C6 O3 -179.04(10) . . . . ?
C4B C5 C6 C7 -0.31(16) . . . . ?
C4B C8A C9 C9A -0.13(12) . . . . ?
C4B C8A C9 C10 119.00(11) . . . . ?
C4B C8A C9 C11 -117.74(11) . . . . ?
C4A C4B C5 C6 177.04(11) . . . . ?
C4A C4B C8A C8 -177.44(10) . . . . ?
C4A C4B C8A C9 1.04(13) . . . . ?
C4 C4A C9A C1 1.27(17) . . . . ?
C4 C4A C9A C9 -178.63(10) . . . . ?
C5 C4B C4A C4 0.5(2) . . . . ?
C5 C4B C4A C9A -179.67(11) . . . . ?
C5 C4B C8A C8 0.81(17) . . . . ?
C5 C4B C8A C9 179.29(10) . . . . ?
C5 C6 C7 C8 1.44(17) . . . . ?
C5 C6 C7 C17 -175.86(10) . . . . ?
C6 C7 C8 C8A -1.44(17) . . . . ?
C6 C7 C17 O4 175.97(10) . . . . ?
C6 C7 C17 N2 -1.42(17) . . . . ?
C7 C8 C8A C4B 0.34(17) . . . . ?
C7 C8 C8A C9 -177.84(11) . . . . ?
C8 C7 C17 O4 -1.31(16) . . . . ?
C8 C7 C17 N2 -178.69(11) . . . . ?
C8 C8A C9 C9A 178.16(12) . . . . ?
C8 C8A C9 C10 -62.71(16) . . . . ?
C8 C8A C9 C11 60.55(16) . . . . ?
C8A C4B C4A C4 178.60(11) . . . . ?
C8A C4B C4A C9A -1.60(13) . . . . ?
C8A C4B C5 C6 -0.81(17) . . . . ?
C8A C9 C9A C1 179.23(12) . . . . ?
C8A C9 C9A C4A -0.88(12) . . . . ?
C9A C1 C2 C3 -0.78(17) . . . . ?
C9A C1 C2 C12 176.34(11) . . . . ?
C9A C4A C4 C3 -0.94(17) . . . . ?
C10 C9 C9A C1 60.76(16) . . . . ?
C10 C9 C9A C4A -119.35(11) . . . . ?
C11 C9 C9A C1 -62.62(16) . . . . ?
C11 C9 C9A C4A 117.26(11) . . . . ?
C12 O2 C13 C14 -6.63(13) . . . . ?
C12 N1 C14 C13 -5.31(13) . . . . ?
C12 N1 C14 C15 113.95(11) . . . . ?
C12 N1 C14 C16 -124.66(11) . . . . ?
C12 C2 C3 O1 2.98(16) . . . . ?
C12 C2 C3 C4 -176.07(10) . . . . ?
C13 O2 C12 N1 3.64(14) . . . . ?
C13 O2 C12 C2 -174.89(11) . . . . ?
C14 N1 C12 O2 1.32(14) . . . . ?
C14 N1 C12 C2 179.75(10) . . . . ?
C17 O4 C18 C19 16.21(12) . . . . ?
C17 N2 C19 C18 13.50(12) . . . . ?
C17 N2 C19 C20 -104.62(11) . . . . ?
C17 N2 C19 C21 132.95(10) . . . . ?
C17 C7 C8 C8A 175.79(10) . . . . ?
C18 O4 C17 N2 -8.52(14) . . . . ?
C18 O4 C17 C7 173.90(10) . . . . ?
C19 N2 C17 O4 -3.76(14) . . . . ?
C19 N2 C17 C7 173.61(10) . . . . ?
