#------------------------------------------------------------------------------
#$Date: 2019-11-17 15:36:41 +0200 (Sun, 17 Nov 2019) $
#$Revision: 230922 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/22/97/7229707.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_7229707
loop_
_publ_author_name
'Fuentes Pineda, Rosinda'
'Troughton, Joel'
'Planells, Miquel'
'Sanchez-Molina Santos, Irene'
'Muhith, Farmin'
'Nichol, Gary S.'
'Haque, Saif'
'Watson, Trystan'
'Robertson, Neil'
_publ_section_title
;
 Effect of alkyl chain length on the properties of triphenylamine-based
 hole transport materials and their performance in perovskite solar cells.
;
_journal_issue                   2
_journal_name_full               'Physical chemistry chemical physics : PCCP'
_journal_page_first              1252
_journal_page_last               1260
_journal_paper_doi               10.1039/c7cp07682g
_journal_volume                  20
_journal_year                    2018
_chemical_formula_moiety         'C56 H60 N2 O4'
_chemical_formula_sum            'C56 H60 N2 O4'
_chemical_formula_weight         825.06
_chemical_name_systematic        BuO-DATPA
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             2015-08-13
_audit_creation_method
;
Olex2 1.2-beta
(compiled 2015.01.26 svn.r3150 for OlexSys, GUI svn.r4998)
;
_audit_update_record
;
2017-09-15 deposited with the CCDC.
2017-12-11 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 93.5009(5)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   11.82431(7)
_cell_length_b                   13.11889(7)
_cell_length_c                   14.97854(9)
_cell_measurement_reflns_used    35031
_cell_measurement_temperature    120.0
_cell_measurement_theta_max      75.9980
_cell_measurement_theta_min      4.4480
_cell_volume                     2319.16(2)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35e (release 07-10-2014 CrysAlis171 .NET)
(compiled Oct  7 2014,17:20:27)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35e (release 07-10-2014 CrysAlis171 .NET)
(compiled Oct  7 2014,17:20:27)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35e (release 07-10-2014 CrysAlis171 .NET)
(compiled Oct  7 2014,17:20:27)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      120.0
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.1574
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_details
;
#__ type_ start__ end____ width___ exp.time_
  1 omega  -50.00   29.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      -43.1686   38.0000  -90.0000 79

#__ type_ start__ end____ width___ exp.time_
  2 omega  -70.00   27.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      -43.1686   57.0000  120.0000 97

#__ type_ start__ end____ width___ exp.time_
  3 omega -113.00  -17.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      -43.1686  -57.0000  -30.0000 96

#__ type_ start__ end____ width___ exp.time_
  4 omega  -50.00   29.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      -43.1686   38.0000 -120.0000 79

#__ type_ start__ end____ width___ exp.time_
  5 omega    1.00   83.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       43.1686  -99.0000 -120.0000 82

#__ type_ start__ end____ width___ exp.time_
  6 omega   23.00   98.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       43.1686 -125.0000 -180.0000 75

#__ type_ start__ end____ width___ exp.time_
  7 omega   40.00   99.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      111.0000  -45.0000  -30.0000 59

#__ type_ start__ end____ width___ exp.time_
  8 omega   30.00  109.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      111.0000  -94.0000 -180.0000 79

#__ type_ start__ end____ width___ exp.time_
  9 omega   37.00  142.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      111.0000  -77.0000   90.0000 105

#__ type_ start__ end____ width___ exp.time_
 10 omega   39.00  121.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      111.0000 -125.0000    0.0000 82

#__ type_ start__ end____ width___ exp.time_
 11 omega   39.00  121.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      111.0000 -125.0000   90.0000 82

#__ type_ start__ end____ width___ exp.time_
 12 omega   83.00  178.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      111.0000   61.0000  -90.0000 95

#__ type_ start__ end____ width___ exp.time_
 13 omega   94.00  178.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      111.0000  125.0000 -150.0000 84

#__ type_ start__ end____ width___ exp.time_
 14 omega   39.00  121.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      111.0000 -125.0000 -180.0000 82

#__ type_ start__ end____ width___ exp.time_
 15 omega   30.00  109.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      111.0000  -94.0000    0.0000 79

#__ type_ start__ end____ width___ exp.time_
 16 omega   36.00   91.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      111.0000  -30.0000  120.0000 55

#__ type_ start__ end____ width___ exp.time_
 17 omega   36.00   91.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      111.0000  -30.0000   30.0000 55

#__ type_ start__ end____ width___ exp.time_
 18 omega   36.00   91.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      111.0000  -30.0000 -150.0000 55

#__ type_ start__ end____ width___ exp.time_
 19 omega   41.00  139.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      111.0000  -61.0000  -90.0000 98

#__ type_ start__ end____ width___ exp.time_
 20 omega   30.00  109.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      111.0000  -94.0000 -120.0000 79

#__ type_ start__ end____ width___ exp.time_
 21 omega   36.00   91.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      111.0000  -30.0000  -60.0000 55

#__ type_ start__ end____ width___ exp.time_
 22 omega   40.00   99.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      111.0000  -45.0000   60.0000 59

#__ type_ start__ end____ width___ exp.time_
 23 omega   39.00  121.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      111.0000 -125.0000  120.0000 82

#__ type_ start__ end____ width___ exp.time_
 24 omega   36.00   91.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      111.0000  -30.0000 -180.0000 55

#__ type_ start__ end____ width___ exp.time_
 25 omega   87.00  178.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      111.0000   30.0000   90.0000 91

#__ type_ start__ end____ width___ exp.time_
 26 omega   39.00  121.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      111.0000 -125.0000  -60.0000 82

#__ type_ start__ end____ width___ exp.time_
 27 omega   94.00  178.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      111.0000  125.0000  -60.0000 84

#__ type_ start__ end____ width___ exp.time_
 28 omega   30.00  109.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      111.0000  -94.0000  -60.0000 79

#__ type_ start__ end____ width___ exp.time_
 29 omega   36.00   91.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      111.0000  -30.0000  -30.0000 55

#__ type_ start__ end____ width___ exp.time_
 30 omega   24.00  178.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      111.0000    0.0000 -120.0000 154

#__ type_ start__ end____ width___ exp.time_
 31 omega  -50.00   29.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      -43.1686   38.0000   30.0000 79

#__ type_ start__ end____ width___ exp.time_
 32 omega -117.00  -12.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      -43.1686  -77.0000 -120.0000 105

#__ type_ start__ end____ width___ exp.time_
 33 omega -117.00  -12.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      -43.1686  -77.0000  150.0000 105

#__ type_ start__ end____ width___ exp.time_
 34 omega -117.00  -12.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      -43.1686  -77.0000   60.0000 105

#__ type_ start__ end____ width___ exp.time_
 35 omega -122.00   -6.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      -43.1686  -19.0000  -30.0000 116

#__ type_ start__ end____ width___ exp.time_
 36 omega -117.00  -12.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      -43.1686  -77.0000  -30.0000 105

#__ type_ start__ end____ width___ exp.time_
 37 omega   21.00  116.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       43.1686   38.0000  120.0000 95

#__ type_ start__ end____ width___ exp.time_
 38 omega   83.00  178.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      111.0000   61.0000    0.0000 95

#__ type_ start__ end____ width___ exp.time_
 39 omega   80.00  178.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      111.0000   77.0000   90.0000 98

#__ type_ start__ end____ width___ exp.time_
 40 omega   82.00  178.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      111.0000   69.0000 -157.9918 96

#__ type_ start__ end____ width___ exp.time_
 41 omega   83.00  178.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      111.0000   61.0000  150.0000 95

#__ type_ start__ end____ width___ exp.time_
 42 omega   83.00  178.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      111.0000   61.0000  -60.0000 95

#__ type_ start__ end____ width___ exp.time_
 43 omega   83.00  178.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      111.0000   61.0000   30.0000 95

#__ type_ start__ end____ width___ exp.time_
 44 omega   83.00  149.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      111.0000   61.0000 -120.0000 66

#__ type_ start__ end____ width___ exp.time_
 45 omega   87.00  178.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      111.0000   30.0000    0.0000 91
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Rigaku Oxford Diffraction SuperNova'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      0.0824241000
_diffrn_orient_matrix_UB_12      0.0135858000
_diffrn_orient_matrix_UB_13      0.0828120000
_diffrn_orient_matrix_UB_21      0.0477138000
_diffrn_orient_matrix_UB_22      0.0971869000
_diffrn_orient_matrix_UB_23      -0.0415284000
_diffrn_orient_matrix_UB_31      -0.0892862000
_diffrn_orient_matrix_UB_32      0.0644959000
_diffrn_orient_matrix_UB_33      0.0450901000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0378
_diffrn_reflns_av_unetI/netI     0.0132
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            56181
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         76.172
_diffrn_reflns_theta_min         3.745
_diffrn_source                   'sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.572
_exptl_absorpt_correction_T_max  0.997
_exptl_absorpt_correction_T_min  0.995
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35e (release 07-10-2014 CrysAlis171 .NET)
(compiled Oct  7 2014,17:20:27)
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            orange
_exptl_crystal_colour_primary    orange
_exptl_crystal_density_diffrn    1.181
_exptl_crystal_description       block
_exptl_crystal_F_000             884
_exptl_crystal_recrystallization_method
'The material was recrystallised from benzene by slow evaporation'
_exptl_crystal_size_max          0.2453
_exptl_crystal_size_mid          0.2376
_exptl_crystal_size_min          0.1394
_refine_diff_density_max         0.472
_refine_diff_density_min         -0.389
_refine_diff_density_rms         0.043
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.028
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     320
_refine_ls_number_reflns         4833
_refine_ls_number_restraints     45
_refine_ls_restrained_S_all      1.061
_refine_ls_R_factor_all          0.0598
_refine_ls_R_factor_gt           0.0578
_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)+(0.0871P)²+0.9714P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1536
_refine_ls_wR_factor_ref         0.1559
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4563
_reflns_number_total             4833
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            c7cp07682g2.cif
_cod_data_source_block           nr15007
_cod_depositor_comments
'Adding full bibliography for 7229705--7229708.cif.'
_cod_database_code               7229707
_chemical_oxdiff_formula         'C56 H60 N2 O4'
_chemical_oxdiff_usercomment     '@ 120 K BuO_DATPA'
_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.
;
_reflns_odcompleteness_completeness 99.72
_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
 At 1.5 times of:
  All C(H,H,H) groups
2. Rigid body (RIGU) restrains
 C16, C26, C27, C30
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
 C16A, C26A, C27A, C30A
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
3. Same fragment restrains
{C17, C28, C29, C31} sigma for 1-2: 0.02, 1-3: 0.02
as
{C16, C26, C27, C30}
{C17, C28, C29, C31} sigma for 1-2: 0.02, 1-3: 0.02
as
{C16A, C26A, C27A, C30A}
4. Others
 Sof(C16A)=Sof(H16C)=Sof(H16D)=Sof(C26A)=Sof(H26C)=Sof(H26D)=Sof(C27A)=
 Sof(H27C)=Sof(H27D)=Sof(C30A)=Sof(H30D)=Sof(H30E)=Sof(H30F)=1-FVAR(1)
 Sof(C16)=Sof(H16A)=Sof(H16B)=Sof(C26)=Sof(H26A)=Sof(H26B)=Sof(C27)=Sof(H27A)=
 Sof(H27B)=Sof(C30)=Sof(H30A)=Sof(H30B)=Sof(H30C)=FVAR(1)
5.a Secondary CH2 refined with riding coordinates:
 C16(H16A,H16B), C26(H26A,H26B), C27(H27A,H27B), C16A(H16C,H16D), C26A(H26C,
 H26D), C27A(H27C,H27D), C17(H17A,H17B), C28(H28A,H28B), C29(H29A,H29B)
5.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C5(H5), C6(H6), C9(H9), C10(H10), C12(H12), C13(H13),
 C19(H19), C20(H20), C22(H22), C23(H23)
5.c Idealised Me refined as rotating group:
 C30(H30A,H30B,H30C), C30A(H30D,H30E,H30F), C31(H31A,H31B,H31C)
;
_shelx_shelxl_version_number     2014/7
_olex2_date_sample_data_collection 2015-06-12
_olex2_date_sample_submission    2015-06-01
_olex2_diffrn_ambient_temperature_device 'Oxford Cryosystems Cryostream 700+'
_olex2_exptl_crystal_mounting_method
'The crystal was mounted on a MITIGEN holder in Paratone oil'
_olex2_submission_original_sample_id BuO_DATPA
_olex2_submission_special_instructions 'No special instructions were received'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, 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
O14 O 0.62428(8) 0.62450(8) 0.63142(7) 0.0348(2) Uani 1 1 d . . . . .
O15 O 0.75360(13) -0.03555(10) 0.88641(10) 0.0619(4) Uani 1 1 d . . . . .
N7 N 0.90202(11) 0.36429(10) 0.84263(10) 0.0423(3) Uani 1 1 d . . . . .
C1 C 0.68696(12) 0.56082(10) 0.68680(9) 0.0311(3) Uani 1 1 d . . . . .
C2 C 0.79807(12) 0.54429(11) 0.66368(10) 0.0337(3) Uani 1 1 d . . . . .
H2 H 0.8248 0.5765 0.6122 0.040 Uiso 1 1 calc R . . . .
C3 C 0.86931(12) 0.48140(11) 0.71528(11) 0.0375(3) Uani 1 1 d . . . . .
H3 H 0.9448 0.4706 0.6991 0.045 Uiso 1 1 calc R . . . .
C4 C 0.83114(12) 0.43363(11) 0.79099(10) 0.0374(3) Uani 1 1 d . . . . .
C5 C 0.72111(12) 0.45117(12) 0.81436(10) 0.0367(3) Uani 1 1 d . . . . .
H5 H 0.6949 0.4196 0.8663 0.044 Uiso 1 1 calc R . . . .
C6 C 0.64846(12) 0.51427(11) 0.76287(10) 0.0346(3) Uani 1 1 d . . . . .
H6 H 0.5732 0.5255 0.7795 0.042 Uiso 1 1 calc R . . . .
C8 C 0.86350(12) 0.26205(11) 0.85151(10) 0.0362(3) Uani 1 1 d . . . . .
C9 C 0.87608(14) 0.21227(12) 0.93343(10) 0.0393(3) Uani 1 1 d . . . . .
H9 H 0.9098 0.2472 0.9839 0.047 Uiso 1 1 calc R . . . .
C10 C 0.84024(15) 0.11290(12) 0.94259(11) 0.0428(4) Uani 1 1 d . . . . .
H10 H 0.8509 0.0795 0.9987 0.051 Uiso 1 1 calc R . . . .
C11 C 0.78851(14) 0.06149(12) 0.86986(11) 0.0428(4) Uani 1 1 d . . . . .
C12 C 0.77429(14) 0.11077(14) 0.78810(11) 0.0449(4) Uani 1 1 d . . . . .
H12 H 0.7384 0.0766 0.7381 0.054 Uiso 1 1 calc R . . . .
C13 C 0.81258(13) 0.21012(13) 0.77930(10) 0.0413(4) Uani 1 1 d . . . . .
H13 H 0.8037 0.2430 0.7228 0.050 Uiso 1 1 calc R . . . .
C16 C 0.7162(5) -0.1027(3) 0.8204(3) 0.0655(13) Uani 0.699(7) 1 d D U P A 1
H16A H 0.7670 -0.0989 0.7704 0.079 Uiso 0.699(7) 1 calc R . P A 1
H16B H 0.6393 -0.0824 0.7972 0.079 Uiso 0.699(7) 1 calc R . P A 1
C26 C 0.7129(3) -0.2121(2) 0.8542(4) 0.0697(13) Uani 0.699(7) 1 d D U P A 1
H26A H 0.6777 -0.2118 0.9125 0.084 Uiso 0.699(7) 1 calc R . P A 1
H26B H 0.6626 -0.2518 0.8119 0.084 Uiso 0.699(7) 1 calc R . P A 1
C27 C 0.8180(4) -0.2641(4) 0.8654(5) 0.0969(19) Uani 0.699(7) 1 d D U P A 1
H27A H 0.8184 -0.2914 0.9270 0.116 Uiso 0.699(7) 1 calc R . P A 1
H27B H 0.8079 -0.3241 0.8256 0.116 Uiso 0.699(7) 1 calc R . P A 1
C30 C 0.9283(4) -0.2356(4) 0.8565(4) 0.116(2) Uani 0.699(7) 1 d D U P A 1
H30A H 0.9407 -0.1672 0.8815 0.174 Uiso 0.699(7) 1 calc GR . P A 1
H30B H 0.9440 -0.2352 0.7930 0.174 Uiso 0.699(7) 1 calc GR . P A 1
H30C H 0.9790 -0.2841 0.8886 0.174 Uiso 0.699(7) 1 calc GR . P A 1
C16A C 0.7228(7) -0.0835(6) 0.7886(5) 0.0316(15) Uani 0.301(7) 1 d D U P A 2
H16C H 0.6633 -0.0436 0.7548 0.038 Uiso 0.301(7) 1 calc R . P A 2
H16D H 0.7904 -0.0889 0.7530 0.038 Uiso 0.301(7) 1 calc R . P A 2
C26A C 0.6801(6) -0.1869(5) 0.8149(4) 0.0401(16) Uani 0.301(7) 1 d D U P A 2
H26C H 0.6015 -0.1796 0.8333 0.048 Uiso 0.301(7) 1 calc R . P A 2
H26D H 0.6778 -0.2319 0.7617 0.048 Uiso 0.301(7) 1 calc R . P A 2
C27A C 0.7489(7) -0.2370(5) 0.8882(4) 0.046(2) Uani 0.301(7) 1 d D U P A 2
H27C H 0.7398 -0.1974 0.9435 0.056 Uiso 0.301(7) 1 calc R . P A 2
H27D H 0.7163 -0.3054 0.8975 0.056 Uiso 0.301(7) 1 calc R . P A 2
C30A C 0.8705(8) -0.2496(6) 0.8780(8) 0.066(3) Uani 0.301(7) 1 d D U P A 2
H30D H 0.9031 -0.1845 0.8605 0.099 Uiso 0.301(7) 1 calc GR . P A 2
H30E H 0.8822 -0.3007 0.8317 0.099 Uiso 0.301(7) 1 calc GR . P A 2
H30F H 0.9076 -0.2722 0.9349 0.099 Uiso 0.301(7) 1 calc GR . P A 2
C17 C 0.50733(12) 0.63932(11) 0.64848(10) 0.0349(3) Uani 1 1 d D . . . .
H17A H 0.5009 0.6739 0.7067 0.042 Uiso 1 1 calc R . . . .
H17B H 0.4679 0.5728 0.6503 0.042 Uiso 1 1 calc R . . . .
C28 C 0.45504(13) 0.70443(11) 0.57345(10) 0.0366(3) Uani 1 1 d D . . . .
H28A H 0.5016 0.7666 0.5678 0.044 Uiso 1 1 calc R . . . .
H28B H 0.3785 0.7261 0.5891 0.044 Uiso 1 1 calc R . . . .
C29 C 0.44528(15) 0.65000(13) 0.48363(11) 0.0429(4) Uani 1 1 d D . . . .
H29A H 0.3982 0.5881 0.4888 0.051 Uiso 1 1 calc R . . . .
H29B H 0.5216 0.6282 0.4676 0.051 Uiso 1 1 calc R . . . .
C31 C 0.39287(19) 0.71769(16) 0.40962(12) 0.0579(5) Uani 1 1 d D . . . .
H31A H 0.4406 0.7780 0.4030 0.087 Uiso 1 1 calc GR . . . .
H31B H 0.3171 0.7391 0.4250 0.087 Uiso 1 1 calc GR . . . .
H31C H 0.3872 0.6796 0.3532 0.087 Uiso 1 1 calc GR . . . .
C18 C 1.01312(12) 0.39077(12) 0.87091(10) 0.0375(3) Uani 1 1 d . . . . .
C19 C 1.04124(12) 0.49161(12) 0.89291(11) 0.0378(3) Uani 1 1 d . . . . .
H19 H 0.9845 0.5429 0.8875 0.045 Uiso 1 1 calc R . . . .
C20 C 1.15026(12) 0.51752(12) 0.92242(10) 0.0375(3) Uani 1 1 d . . . . .
H20 H 1.1676 0.5864 0.9373 0.045 Uiso 1 1 calc R . . . .
C21 C 1.23589(12) 0.44339(12) 0.93071(10) 0.0376(3) Uani 1 1 d . . . . .
C22 C 1.20770(13) 0.34293(12) 0.90846(11) 0.0419(4) Uani 1 1 d . . . . .
H22 H 1.2645 0.2917 0.9135 0.050 Uiso 1 1 calc R . . . .
C23 C 1.09868(13) 0.31678(12) 0.87933(12) 0.0427(4) Uani 1 1 d . . . . .
H23 H 1.0813 0.2478 0.8648 0.051 Uiso 1 1 calc R . . . .
C24 C 1.34919(13) 0.46956(12) 0.96022(11) 0.0394(3) Uani 1 1 d . . . . .
C25 C 1.44553(12) 0.48889(12) 0.98527(10) 0.0389(3) Uani 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_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
_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
-4 1 5 0.1232 -4.0000 1.0000 5.0000 0.0979 -0.3013 0.6471
1 -5 2 0.1239 1.0000 -5.0000 2.0000 0.1801 -0.5213 -0.3216
3 0 -5 0.0996 3.0000 0.0000 -5.0000 -0.1668 0.3508 -0.4933
-1 5 -3 0.0985 -1.0000 5.0000 -3.0000 -0.2629 0.5628 0.2765
3 2 5 0.0509 3.0000 2.0000 5.0000 0.6885 0.1299 0.0866
-5 2 0 0.1056 -5.0000 2.0000 -0.0000 -0.3849 -0.0442 0.5754
-2 -2 -5 0.0807 -2.0000 -2.0000 -5.0000 -0.6061 -0.0822 -0.1759
1 -3 -5 0.1118 1.0000 -3.0000 -5.0000 -0.3724 -0.0362 -0.5082
-5 0 -4 0.1026 -5.0000 0.0000 -4.0000 -0.7434 -0.0725 0.2661
-5 4 4 0.1377 -5.0000 4.0000 4.0000 -0.0265 -0.0159 0.8848
5 -2 0 0.1420 5.0000 -2.0000 0.0000 0.3849 0.0442 -0.5754
-2 -3 5 0.1504 -2.0000 -3.0000 5.0000 0.2085 -0.5946 0.2105
1 5 -5 0.1033 1.0000 5.0000 -5.0000 -0.2637 0.7413 0.0077
-1 -5 0 0.1099 -1.0000 -5.0000 0.0000 -0.1504 -0.5336 -0.2332
-5 -5 3 0.1250 -5.0000 -5.0000 3.0000 -0.2316 -0.8491 0.2592
-5 0 4 0.1153 -5.0000 -0.0000 4.0000 -0.0809 -0.4047 0.6268
-5 -1 -1 0.0895 -5.0000 -1.0000 -1.0000 -0.5085 -0.2942 0.3368
-4 -5 -5 0.0859 -4.0000 -5.0000 -5.0000 -0.8117 -0.4691 -0.1908
0 -1 -5 0.0909 0.0000 -1.0000 -5.0000 -0.4276 0.1105 -0.2899
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_3
C1 O14 C17 117.94(11) .
C11 O15 C16 123.6(3) .
C11 O15 C16A 104.6(3) .
C8 N7 C4 117.94(12) .
C18 N7 C4 120.91(12) .
C18 N7 C8 120.32(12) .
O14 C1 C2 115.40(12) .
O14 C1 C6 124.98(13) .
C6 C1 C2 119.61(13) .
C1 C2 H2 119.8 .
C3 C2 C1 120.33(13) .
C3 C2 H2 119.8 .
C2 C3 H3 119.8 .
C2 C3 C4 120.45(13) .
C4 C3 H3 119.8 .
C3 C4 N7 121.14(13) .
C5 C4 N7 119.76(13) .
C5 C4 C3 119.06(13) .
C4 C5 H5 119.5 .
C4 C5 C6 121.04(13) .
C6 C5 H5 119.5 .
C1 C6 H6 120.3 .
C5 C6 C1 119.50(13) .
C5 C6 H6 120.3 .
C9 C8 N7 120.46(14) .
C13 C8 N7 121.08(14) .
C13 C8 C9 118.46(14) .
C8 C9 H9 119.5 .
C10 C9 C8 120.97(14) .
C10 C9 H9 119.5 .
C9 C10 H10 119.9 .
C9 C10 C11 120.21(15) .
C11 C10 H10 119.9 .
O15 C11 C10 115.67(15) .
O15 C11 C12 125.00(15) .
C12 C11 C10 119.32(15) .
C11 C12 H12 120.0 .
C11 C12 C13 119.94(15) .
C13 C12 H12 120.0 .
C8 C13 C12 121.09(14) .
C8 C13 H13 119.5 .
C12 C13 H13 119.5 .
O15 C16 H16A 109.2 .
O15 C16 H16B 109.2 .
O15 C16 C26 112.3(3) .
H16A C16 H16B 107.9 .
C26 C16 H16A 109.2 .
C26 C16 H16B 109.2 .
C16 C26 H26A 108.1 .
C16 C26 H26B 108.1 .
H26A C26 H26B 107.3 .
C27 C26 C16 116.9(4) .
C27 C26 H26A 108.1 .
C27 C26 H26B 108.1 .
C26 C27 H27A 103.8 .
C26 C27 H27B 103.8 .
H27A C27 H27B 105.4 .
C30 C27 C26 133.6(4) .
C30 C27 H27A 103.8 .
C30 C27 H27B 103.8 .
C27 C30 H30A 109.5 .
C27 C30 H30B 109.5 .
C27 C30 H30C 109.5 .
H30A C30 H30B 109.5 .
H30A C30 H30C 109.5 .
H30B C30 H30C 109.5 .
O15 C16A H16C 111.8 .
O15 C16A H16D 111.8 .
H16C C16A H16D 109.5 .
C26A C16A O15 100.0(4) .
C26A C16A H16C 111.8 .
C26A C16A H16D 111.8 .
C16A C26A H26C 108.6 .
C16A C26A H26D 108.6 .
H26C C26A H26D 107.6 .
C27A C26A C16A 114.5(6) .
C27A C26A H26C 108.6 .
C27A C26A H26D 108.6 .
C26A C27A H27C 107.8 .
C26A C27A H27D 107.8 .
H27C C27A H27D 107.1 .
C30A C27A C26A 118.2(6) .
C30A C27A H27C 107.8 .
C30A C27A H27D 107.8 .
C27A C30A H30D 109.5 .
C27A C30A H30E 109.5 .
C27A C30A H30F 109.5 .
H30D C30A H30E 109.5 .
H30D C30A H30F 109.5 .
H30E C30A H30F 109.5 .
O14 C17 H17A 110.2 .
O14 C17 H17B 110.2 .
O14 C17 C28 107.39(11) .
H17A C17 H17B 108.5 .
C28 C17 H17A 110.2 .
C28 C17 H17B 110.2 .
C17 C28 H28A 108.9 .
C17 C28 H28B 108.9 .
C17 C28 C29 113.41(12) .
H28A C28 H28B 107.7 .
C29 C28 H28A 108.9 .
C29 C28 H28B 108.9 .
C28 C29 H29A 109.2 .
C28 C29 H29B 109.2 .
C28 C29 C31 112.07(14) .
H29A C29 H29B 107.9 .
C31 C29 H29A 109.2 .
C31 C29 H29B 109.2 .
C29 C31 H31A 109.5 .
C29 C31 H31B 109.5 .
C29 C31 H31C 109.5 .
H31A C31 H31B 109.5 .
H31A C31 H31C 109.5 .
H31B C31 H31C 109.5 .
N7 C18 C23 120.95(15) .
C19 C18 N7 120.76(13) .
C19 C18 C23 118.28(14) .
C18 C19 H19 119.6 .
C20 C19 C18 120.84(13) .
C20 C19 H19 119.6 .
C19 C20 H20 119.6 .
C19 C20 C21 120.83(15) .
C21 C20 H20 119.6 .
C20 C21 C24 121.28(15) .
C22 C21 C20 118.21(14) .
C22 C21 C24 120.50(13) .
C21 C22 H22 119.5 .
C23 C22 C21 121.06(14) .
C23 C22 H22 119.5 .
C18 C23 H23 119.6 .
C22 C23 C18 120.78(15) .
C22 C23 H23 119.6 .
C25 C24 C21 178.23(17) .
C24 C25 C25 179.3(2) 3_867
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
O14 C1 1.3638(16) .
O14 C17 1.4348(17) .
O15 C11 1.366(2) .
O15 C16 1.376(4) .
O15 C16A 1.616(8) .
N7 C4 1.4315(18) .
N7 C8 1.425(2) .
N7 C18 1.399(2) .
C1 C2 1.396(2) .
C1 C6 1.394(2) .
C2 H2 0.9500 .
C2 C3 1.381(2) .
C3 H3 0.9500 .
C3 C4 1.395(2) .
C4 C5 1.387(2) .
C5 H5 0.9500 .
C5 C6 1.392(2) .
C6 H6 0.9500 .
C8 C9 1.390(2) .
C8 C13 1.384(2) .
C9 H9 0.9500 .
C9 C10 1.380(2) .
C10 H10 0.9500 .
C10 C11 1.391(2) .
C11 C12 1.386(2) .
C12 H12 0.9500 .
C12 C13 1.389(3) .
C13 H13 0.9500 .
C16 H16A 0.9900 .
C16 H16B 0.9900 .
C16 C26 1.523(5) .
C26 H26A 0.9900 .
C26 H26B 0.9900 .
C26 C27 1.418(5) .
C27 H27A 0.9900 .
C27 H27B 0.9900 .
C27 C30 1.371(6) .
C30 H30A 0.9800 .
C30 H30B 0.9800 .
C30 H30C 0.9800 .
C16A H16C 0.9900 .
C16A H16D 0.9900 .
C16A C26A 1.508(7) .
C26A H26C 0.9900 .
C26A H26D 0.9900 .
C26A C27A 1.480(9) .
C27A H27C 0.9900 .
C27A H27D 0.9900 .
C27A C30A 1.464(10) .
C30A H30D 0.9800 .
C30A H30E 0.9800 .
C30A H30F 0.9800 .
C17 H17A 0.9900 .
C17 H17B 0.9900 .
C17 C28 1.5131(19) .
C28 H28A 0.9900 .
C28 H28B 0.9900 .
C28 C29 1.521(2) .
C29 H29A 0.9900 .
C29 H29B 0.9900 .
C29 C31 1.522(2) .
C31 H31A 0.9800 .
C31 H31B 0.9800 .
C31 H31C 0.9800 .
C18 C19 1.399(2) .
C18 C23 1.402(2) .
C19 H19 0.9500 .
C19 C20 1.379(2) .
C20 H20 0.9500 .
C20 C21 1.404(2) .
C21 C22 1.395(2) .
C21 C24 1.427(2) .
C22 H22 0.9500 .
C22 C23 1.379(2) .
C23 H23 0.9500 .
C24 C25 1.204(2) .
C25 C25 1.367(3) 3_867
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
O14 C1 C2 C3 179.77(13)
O14 C1 C6 C5 -179.60(13)
O14 C17 C28 C29 68.71(16)
O15 C11 C12 C13 179.49(15)
O15 C16 C26 C27 -76.8(6)
O15 C16A C26A C27A -42.9(7)
N7 C4 C5 C6 -176.81(14)
N7 C8 C9 C10 -179.27(15)
N7 C8 C13 C12 -179.52(14)
N7 C18 C19 C20 178.77(14)
N7 C18 C23 C22 -179.05(15)
C1 O14 C17 C28 -174.81(11)
C1 C2 C3 C4 0.0(2)
C2 C1 C6 C5 -0.6(2)
C2 C3 C4 N7 176.85(14)
C2 C3 C4 C5 -0.8(2)
C3 C4 C5 C6 0.9(2)
C4 N7 C8 C9 -137.97(15)
C4 N7 C8 C13 41.8(2)
C4 N7 C18 C19 33.7(2)
C4 N7 C18 C23 -147.39(16)
C4 C5 C6 C1 -0.2(2)
C6 C1 C2 C3 0.6(2)
C8 N7 C4 C3 -119.96(17)
C8 N7 C4 C5 57.7(2)
C8 N7 C18 C19 -156.97(15)
C8 N7 C18 C23 22.0(2)
C8 C9 C10 C11 -1.3(3)
C9 C8 C13 C12 0.3(2)
C9 C10 C11 O15 -178.41(16)
C9 C10 C11 C12 0.6(3)
C10 C11 C12 C13 0.6(2)
C11 O15 C16 C26 164.7(3)
C11 O15 C16A C26A -177.2(4)
C11 C12 C13 C8 -1.1(2)
C13 C8 C9 C10 0.9(2)
C16 O15 C11 C10 -170.1(3)
C16 O15 C11 C12 11.0(4)
C16 C26 C27 C30 3.9(11)
C16A O15 C11 C10 -168.3(3)
C16A O15 C11 C12 12.8(4)
C16A C26A C27A C30A -54.4(8)
C17 O14 C1 C2 176.13(12)
C17 O14 C1 C6 -4.8(2)
C17 C28 C29 C31 -179.75(14)
C18 N7 C4 C3 49.7(2)
C18 N7 C4 C5 -132.72(17)
C18 N7 C8 C9 52.4(2)
C18 N7 C8 C13 -127.83(16)
C18 C19 C20 C21 0.3(2)
C19 C18 C23 C22 -0.1(2)
C19 C20 C21 C22 -0.1(2)
C19 C20 C21 C24 179.30(14)
C20 C21 C22 C23 -0.2(2)
C21 C22 C23 C18 0.3(3)
C23 C18 C19 C20 -0.2(2)
C24 C21 C22 C23 -179.59(15)
