#------------------------------------------------------------------------------
#$Date: 2021-03-05 02:43:19 +0100 (vie 05 de mar de 2021) $
#$Revision: 262555 $
#$URL: svn://www.crystallography.net/cod/cif/7/24/22/7242235.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_7242235
loop_
_publ_author_name
'Humphreys, Joshua'
'Pop, Flavia'
'Hume, Paul A.'
'Murphy, Alanna S.'
'Lewis, William'
'Davies, E. Stephen'
'Argent, Stephen P.'
'Amabilino, David B.'
_publ_section_title
;
 Solid state structure and properties of phenyl diketopyrrolopyrrole
 derivatives
;
_journal_issue                   8
_journal_name_full               CrystEngComm
_journal_page_first              1796
_journal_page_last               1814
_journal_paper_doi               10.1039/D1CE00039J
_journal_volume                  23
_journal_year                    2021
_chemical_absolute_configuration syn
_chemical_formula_moiety         'C28 H32 N2 O4'
_chemical_formula_sum            'C28 H32 N2 O4'
_chemical_formula_weight         460.55
_chemical_name_systematic
'3,6-Bis(4-hydroxyphenyl)-2,5-bis((S)-2-methylbutyl)-2,5- dihydropyrrolo[3,4-c]pyrrole-1,4-dione'
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_date             2019-06-04
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2020-05-26 deposited with the CCDC.	2021-02-04 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 108.388(2)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   11.3208(2)
_cell_length_b                   8.58917(16)
_cell_length_c                   13.1920(3)
_cell_measurement_reflns_used    6351
_cell_measurement_temperature    120(2)
_cell_measurement_theta_max      77.8870
_cell_measurement_theta_min      4.1340
_cell_volume                     1217.25(4)
_computing_cell_refinement       'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_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      'N2 gas'
_diffrn_ambient_temperature      120(2)
_diffrn_crystal_treatment        'flash frozen in gaseous N2'
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_type            'PILATUS3 R 200K Hybrid Pixel Array Detector'
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.981
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -20.00  89.00   0.50    1.50    --    0.00  38.00 120.00  218
  2  ω      8.00  33.00   0.50    1.50    --    0.00 -82.00  60.00   50
  3  ω    -32.00  20.00   0.50    1.50    --    0.00 -19.00 120.00  104
  4  ω    -67.00 -38.00   0.50    1.50    --    0.00 -19.00 120.00   58
  5  ω     10.00  69.00   0.50    6.00    --   99.10 -38.00-150.00  118
  6  ω     41.00  70.00   0.50    6.00    --   99.10 -38.00-180.00   58
  7  ω     38.00  91.00   0.50    6.00    --   99.10 -57.00-120.00  106
  8  ω     53.00  85.00   0.50    6.00    --   99.10 -57.00  30.00   64
  9  ω     66.00  94.00   0.50    6.00    --   99.10 -57.00 120.00   56
 10  ω     74.00 131.00   0.50    6.00    --   99.10  19.00 -30.00  114
 11  ω    125.00 172.00   0.50    6.00    --   99.10  38.00   0.00   94
 12  ω    150.00 188.00   0.50    6.00    --   99.10  19.00 -30.00   76
 13  ω    115.00 141.00   0.50    6.00    --   99.10  19.00  90.00   52
 14  ω     92.00 132.00   0.50    6.00    --   99.10  82.00  30.00   80
 15  ω     89.00 129.00   0.50    6.00    --   99.10  82.00 -60.00   80
 16  ω     90.00 187.00   0.50    6.00    --   99.10  38.00-120.00  194
 17  ω     89.00 115.00   0.50    6.00    --   99.10  77.00-120.00   52
 18  ω     76.00 149.00   0.50    6.00    --   99.10  38.00  90.00  146
 19  ω     82.00 178.00   0.50    6.00    --   99.10  38.00 120.00  192
 20  ω     67.00  97.00   0.50    6.00    --   99.10  19.00  90.00   60
 21  ω     27.00  69.00   0.50    6.00    --   99.10 -38.00 -90.00   84
 22  ω     16.00 119.00   0.50    6.00    --   99.10 -82.00-150.00  206
 23  ω     27.00  53.00   0.50    6.00    --   99.10 -38.00  90.00   52
 24  ω     19.00  86.00   0.50    6.00    --   99.10 -57.00  60.00  134
 25  ω     15.00  66.00   0.50    6.00    --   99.10 -38.00 120.00  102
 26  ω     11.00  39.00   0.50    6.00    --   99.10 -38.00  30.00   56
 27  ω     10.00  60.00   0.50    6.00    --   99.10 -57.00 120.00  100
 28  ω     29.00  63.00   0.50    6.00    --   99.10 -38.00-120.00   68
;
_diffrn_measurement_device       'κ-geometry diffractometer'
_diffrn_measurement_device_type  'XtalLAB PRO MM007, PILATUS3 R 200K'
_diffrn_measurement_method       'ω scans'
_diffrn_measurement_specimen_support 'MiTeGen micromount'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0786771000
_diffrn_orient_matrix_UB_12      0.0081098000
_diffrn_orient_matrix_UB_13      -0.0761927000
_diffrn_orient_matrix_UB_21      0.0815896000
_diffrn_orient_matrix_UB_22      -0.1347568000
_diffrn_orient_matrix_UB_23      0.0610365000
_diffrn_orient_matrix_UB_31      -0.0878472000
_diffrn_orient_matrix_UB_32      -0.1181414000
_diffrn_orient_matrix_UB_33      -0.0748812000
_diffrn_radiation_collimation    'VariMax VHF mirror optic'
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_wavelength_determination fundamental
_diffrn_reflns_av_R_equivalents  0.0400
_diffrn_reflns_av_unetI/netI     0.0470
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.981
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            13621
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.962
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         78.310
_diffrn_reflns_theta_min         4.115
_diffrn_source                   'rotating anode'
_diffrn_source_current           30
_diffrn_source_power             1.2
_diffrn_source_target            Cu
_diffrn_source_type              'MicroMax 007 HF'
_diffrn_source_voltage           40
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.674
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.746
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.46 (Rigaku Oxford Diffraction, 2015)
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 yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.257
_exptl_crystal_description       plate
_exptl_crystal_F_000             492
_exptl_crystal_recrystallization_method
'slow evaporation from an acetone solution at low temperature'
_exptl_crystal_size_max          0.196
_exptl_crystal_size_mid          0.115
_exptl_crystal_size_min          0.061
_refine_diff_density_max         0.166
_refine_diff_density_min         -0.234
_refine_diff_density_rms         0.043
_refine_ls_abs_structure_details
;
 Flack x determined using 1911 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.11(13)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.060
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     313
_refine_ls_number_reflns         5021
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.060
_refine_ls_R_factor_all          0.0452
_refine_ls_R_factor_gt           0.0395
_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)+(0.0423P)²+0.3898P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0997
_refine_ls_wR_factor_ref         0.1042
_reflns_Friedel_coverage         0.833
_reflns_Friedel_fraction_full    0.996
_reflns_Friedel_fraction_max     0.939
_reflns_number_gt                4544
_reflns_number_total             5021
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d1ce00039j2.cif
_cod_data_source_block           PhOHDPP-N-2MB
_cod_depositor_comments
'Adding full bibliography for 7242233--7242239.cif.'
_cod_original_cell_volume        1217.25(5)
_cod_original_sg_symbol_H-M      'P 21'
_cod_database_code               7242235
_shelx_shelxl_version_number     2014/7
_chemical_oxdiff_formula         'C28 H32 N2 O4'
_chemical_oxdiff_usercomment
'MM-592 OJHAMZ #17321 on a micromount for jh/dba'
_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 99.96
_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, All O(H) groups
2.a Ternary CH refined with riding coordinates:
 C25(H20), C20(H25)
2.b Secondary CH2 refined with riding coordinates:
 C24(H19a,H19b), C27(H22a,H22b), C19(H24a,H24b), C22(H27a,H27b)
2.c Aromatic/amide H refined with riding coordinates:
 C10(H2), C8(H3), C9(H5), C11(H6), C14(H14), C16(H15), C17(H17), C15(H18)
2.d Idealised Me refined as rotating group:
 C26(H21a,H21b,H21c), C28(H23a,H23b,H23c), C21(H26a,H26b,H26c), C23(H28a,H28b,
 H28c)
2.e Idealised tetrahedral OH refined as rotating group:
 O3(H1), O4(H4)
;
_nottingham_internal_coll_client JH/DBA
_nottingham_internal_coll_date   30/10/2017
_nottingham_internal_coll_frame_method '\w scans'
_nottingham_internal_coll_frame_time '6.00, 1.50'
_nottingham_internal_coll_frame_width 0.50
_nottingham_internal_coll_instrument 'XtalLAB PRO, A00000876'
_nottingham_internal_coll_location NOTTS
_nottingham_internal_coll_name   OJHAMZ
_nottingham_internal_coll_number 17321
_nottingham_internal_coll_type   custom
_nottingham_internal_coll_user   pcxjh6
_nottingham_internal_process_date 31/10/2017
_nottingham_internal_process_user pcxjh6
_nottingham_internal_refinement_date 31/10/2017
_nottingham_internal_refinement_user pcxjh6
_nottingham_internal_self_validation_date 31/10/2017
_nottingham_internal_self_validation_user pcxjh6
_nottingham_internal_solution_date 31/10/2017
_nottingham_internal_solution_user pcxjh6
_olex2_exptl_crystal_mounting_method 'in fomblin film on a micromount'
_olex2_submission_original_sample_id OJHAMZ
_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
- Detector area scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.776
_oxdiff_exptl_absorpt_empirical_full_min 0.701
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -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 1.2279(2) 0.4839(3) 0.49811(17) 0.0354(5) Uani 1 1 d . . . . .
H1 H 1.2174 0.4146 0.4511 0.053 Uiso 1 1 calc GR . . . .
O2 O 0.72673(18) 0.2112(2) 0.86798(16) 0.0295(4) Uani 1 1 d . . . . .
O3 O 0.83042(18) 0.7958(2) 0.67593(16) 0.0291(4) Uani 1 1 d . . . . .
O4 O 0.25164(18) 0.5174(3) 0.96310(17) 0.0332(5) Uani 1 1 d . . . . .
H4 H 0.2528 0.5838 1.0102 0.050 Uiso 1 1 calc GR . . . .
N1 N 0.8637(2) 0.2818(3) 0.77553(18) 0.0226(5) Uani 1 1 d . . . . .
N2 N 0.6879(2) 0.7227(3) 0.76212(17) 0.0224(5) Uani 1 1 d . . . . .
C1 C 1.1490(2) 0.4590(3) 0.5552(2) 0.0262(6) Uani 1 1 d . . . . .
C2 C 1.0703(3) 0.3306(3) 0.5386(2) 0.0296(6) Uani 1 1 d . . . . .
H2 H 1.0721 0.2546 0.4868 0.035 Uiso 1 1 calc R . . . .
C3 C 0.9897(3) 0.3136(3) 0.5976(2) 0.0277(6) Uani 1 1 d . . . . .
H3 H 0.9363 0.2256 0.5860 0.033 Uiso 1 1 calc R . . . .
C4 C 0.9858(2) 0.4245(3) 0.6740(2) 0.0226(5) Uani 1 1 d . . . . .
C5 C 1.0654(2) 0.5527(3) 0.6896(2) 0.0249(6) Uani 1 1 d . . . . .
H5 H 1.0634 0.6295 0.7408 0.030 Uiso 1 1 calc R . . . .
C6 C 1.1470(3) 0.5695(3) 0.6317(2) 0.0267(6) Uani 1 1 d . . . . .
H6 H 1.2017 0.6562 0.6441 0.032 Uiso 1 1 calc R . . . .
C7 C 0.8953(2) 0.4173(3) 0.7317(2) 0.0222(5) Uani 1 1 d . . . . .
C8 C 0.8207(2) 0.5350(3) 0.7482(2) 0.0228(5) Uani 1 1 d . . . . .
C9 C 0.7381(2) 0.4738(3) 0.7997(2) 0.0227(5) Uani 1 1 d . . . . .
C10 C 0.7679(2) 0.3108(3) 0.8211(2) 0.0225(5) Uani 1 1 d . . . . .
C11 C 0.7877(2) 0.6958(3) 0.7219(2) 0.0223(5) Uani 1 1 d . . . . .
C12 C 0.6562(2) 0.5881(3) 0.8070(2) 0.0222(5) Uani 1 1 d . . . . .
C13 C 0.5513(2) 0.5762(3) 0.8487(2) 0.0229(5) Uani 1 1 d . . . . .
C14 C 0.5339(3) 0.6786(3) 0.9248(2) 0.0284(6) Uani 1 1 d . . . . .
H14 H 0.5911 0.7617 0.9501 0.034 Uiso 1 1 calc R . . . .
C15 C 0.4350(3) 0.6616(3) 0.9640(2) 0.0284(6) Uani 1 1 d . . . . .
H15 H 0.4248 0.7323 1.0160 0.034 Uiso 1 1 calc R . . . .
C16 C 0.3502(2) 0.5408(3) 0.9274(2) 0.0258(6) Uani 1 1 d . . . . .
C17 C 0.3667(3) 0.4375(3) 0.8519(2) 0.0276(6) Uani 1 1 d . . . . .
H17 H 0.3092 0.3548 0.8266 0.033 Uiso 1 1 calc R . . . .
C18 C 0.4663(3) 0.4545(3) 0.8135(2) 0.0248(5) Uani 1 1 d . . . . .
H18 H 0.4771 0.3825 0.7625 0.030 Uiso 1 1 calc R . . . .
C19 C 0.9347(2) 0.1363(3) 0.7960(2) 0.0258(6) Uani 1 1 d . . . . .
H19A H 0.9414 0.0959 0.7278 0.031 Uiso 1 1 calc R . . . .
H19B H 0.8890 0.0583 0.8245 0.031 Uiso 1 1 calc R . . . .
C20 C 1.0654(3) 0.1563(3) 0.8752(2) 0.0273(6) Uani 1 1 d . . . . .
H20 H 1.1089 0.2386 0.8467 0.033 Uiso 1 1 calc R . . . .
C21 C 1.0588(3) 0.2111(4) 0.9829(2) 0.0372(7) Uani 1 1 d . . . . .
H21A H 1.0101 0.3073 0.9734 0.056 Uiso 1 1 calc GR . . . .
H21B H 1.1432 0.2306 1.0310 0.056 Uiso 1 1 calc GR . . . .
H21C H 1.0190 0.1307 1.0137 0.056 Uiso 1 1 calc GR . . . .
C22 C 1.1396(3) 0.0050(4) 0.8846(3) 0.0349(7) Uani 1 1 d . . . . .
H22A H 1.2182 0.0153 0.9445 0.042 Uiso 1 1 calc R . . . .
H22B H 1.0912 -0.0808 0.9024 0.042 Uiso 1 1 calc R . . . .
C23 C 1.1707(3) -0.0387(4) 0.7845(3) 0.0437(8) Uani 1 1 d . . . . .
H23A H 1.0941 -0.0671 0.7279 0.066 Uiso 1 1 calc GR . . . .
H23B H 1.2281 -0.1273 0.7998 0.066 Uiso 1 1 calc GR . . . .
H23C H 1.2098 0.0502 0.7611 0.066 Uiso 1 1 calc GR . . . .
C24 C 0.6255(3) 0.8742(3) 0.7517(2) 0.0271(6) Uani 1 1 d . . . . .
H24A H 0.6782 0.9530 0.7319 0.033 Uiso 1 1 calc R . . . .
H24B H 0.6188 0.9040 0.8222 0.033 Uiso 1 1 calc R . . . .
C25 C 0.4955(3) 0.8788(4) 0.6693(2) 0.0301(6) Uani 1 1 d . . . . .
H25 H 0.4427 0.7978 0.6885 0.036 Uiso 1 1 calc R . . . .
C26 C 0.4398(3) 1.0386(4) 0.6761(3) 0.0478(9) Uani 1 1 d . . . . .
H26A H 0.4424 1.0586 0.7499 0.072 Uiso 1 1 calc GR . . . .
H26B H 0.3533 1.0413 0.6292 0.072 Uiso 1 1 calc GR . . . .
H26C H 0.4880 1.1186 0.6536 0.072 Uiso 1 1 calc GR . . . .
C27 C 0.5012(3) 0.8439(4) 0.5579(3) 0.0384(8) Uani 1 1 d . . . . .
H27A H 0.5515 0.9255 0.5379 0.046 Uiso 1 1 calc R . . . .
H27B H 0.5443 0.7432 0.5596 0.046 Uiso 1 1 calc R . . . .
C28 C 0.3754(3) 0.8362(5) 0.4730(3) 0.0509(10) Uani 1 1 d . . . . .
H28A H 0.3863 0.8119 0.4039 0.076 Uiso 1 1 calc GR . . . .
H28B H 0.3333 0.9368 0.4685 0.076 Uiso 1 1 calc GR . . . .
H28C H 0.3251 0.7548 0.4914 0.076 Uiso 1 1 calc GR . . . .
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
3 3 4 0.0577
-3 -3 -4 0.0577
3 -5 2 0.0616
-3 5 -2 0.0616
-7 2 5 0.0306
7 -2 -5 0.0306
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 O1 H1 109.5 . . ?
C16 O4 H4 109.5 . . ?
C7 N1 C10 111.1(2) . . ?
C7 N1 C19 126.2(2) . . ?
C10 N1 C19 121.3(2) . . ?
C11 N2 C24 122.0(2) . . ?
C12 N2 C11 111.5(2) . . ?
C12 N2 C24 126.5(2) . . ?
O1 C1 C2 122.6(2) . . ?
O1 C1 C6 117.4(2) . . ?
C6 C1 C2 119.9(2) . . ?
C1 C2 H2 120.0 . . ?
C3 C2 C1 120.0(3) . . ?
C3 C2 H2 120.0 . . ?
C2 C3 H3 119.6 . . ?
C2 C3 C4 120.7(3) . . ?
C4 C3 H3 119.6 . . ?
C3 C4 C7 122.3(2) . . ?
C5 C4 C3 118.5(2) . . ?
C5 C4 C7 119.0(2) . . ?
C4 C5 H5 119.5 . . ?
C6 C5 C4 121.0(3) . . ?
C6 C5 H5 119.5 . . ?
C1 C6 H6 120.1 . . ?
C5 C6 C1 119.8(3) . . ?
C5 C6 H6 120.1 . . ?
N1 C7 C4 124.5(2) . . ?
C8 C7 N1 107.3(2) . . ?
C8 C7 C4 128.1(2) . . ?
C7 C8 C9 109.4(2) . . ?
C7 C8 C11 142.1(3) . . ?
C9 C8 C11 108.1(2) . . ?
C8 C9 C10 107.7(2) . . ?
C12 C9 C8 109.2(2) . . ?
C12 C9 C10 143.0(3) . . ?
O2 C10 N1 123.6(2) . . ?
O2 C10 C9 132.0(3) . . ?
N1 C10 C9 104.4(2) . . ?
O3 C11 N2 123.8(2) . . ?
O3 C11 C8 132.2(3) . . ?
N2 C11 C8 104.1(2) . . ?
N2 C12 C13 124.4(2) . . ?
C9 C12 N2 107.0(2) . . ?
C9 C12 C13 128.5(2) . . ?
C14 C13 C12 122.9(2) . . ?
C14 C13 C18 118.2(2) . . ?
C18 C13 C12 118.9(2) . . ?
C13 C14 H14 119.4 . . ?
C15 C14 C13 121.2(3) . . ?
C15 C14 H14 119.4 . . ?
C14 C15 H15 120.0 . . ?
C14 C15 C16 120.0(3) . . ?
C16 C15 H15 120.0 . . ?
O4 C16 C15 122.8(2) . . ?
O4 C16 C17 117.7(2) . . ?
C17 C16 C15 119.4(3) . . ?
C16 C17 H17 119.8 . . ?
C18 C17 C16 120.3(3) . . ?
C18 C17 H17 119.8 . . ?
C13 C18 H18 119.6 . . ?
C17 C18 C13 120.9(2) . . ?
C17 C18 H18 119.6 . . ?
N1 C19 H19A 109.0 . . ?
N1 C19 H19B 109.0 . . ?
N1 C19 C20 112.8(2) . . ?
H19A C19 H19B 107.8 . . ?
C20 C19 H19A 109.0 . . ?
C20 C19 H19B 109.0 . . ?
C19 C20 H20 107.9 . . ?
C19 C20 C22 110.4(2) . . ?
C21 C20 C19 110.6(2) . . ?
C21 C20 H20 107.9 . . ?
C21 C20 C22 112.0(3) . . ?
C22 C20 H20 107.9 . . ?
C20 C21 H21A 109.5 . . ?
C20 C21 H21B 109.5 . . ?
C20 C21 H21C 109.5 . . ?
H21A C21 H21B 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
C20 C22 H22A 108.7 . . ?
C20 C22 H22B 108.7 . . ?
H22A C22 H22B 107.6 . . ?
C23 C22 C20 114.3(3) . . ?
C23 C22 H22A 108.7 . . ?
C23 C22 H22B 108.7 . . ?
C22 C23 H23A 109.5 . . ?
C22 C23 H23B 109.5 . . ?
C22 C23 H23C 109.5 . . ?
H23A C23 H23B 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?
N2 C24 H24A 108.6 . . ?
N2 C24 H24B 108.6 . . ?
N2 C24 C25 114.6(2) . . ?
H24A C24 H24B 107.6 . . ?
C25 C24 H24A 108.6 . . ?
C25 C24 H24B 108.6 . . ?
C24 C25 H25 108.6 . . ?
C26 C25 C24 107.7(3) . . ?
C26 C25 H25 108.6 . . ?
C27 C25 C24 111.0(2) . . ?
C27 C25 H25 108.6 . . ?
C27 C25 C26 112.2(3) . . ?
C25 C26 H26A 109.5 . . ?
C25 C26 H26B 109.5 . . ?
C25 C26 H26C 109.5 . . ?
H26A C26 H26B 109.5 . . ?
H26A C26 H26C 109.5 . . ?
H26B C26 H26C 109.5 . . ?
C25 C27 H27A 108.7 . . ?
C25 C27 H27B 108.7 . . ?
H27A C27 H27B 107.6 . . ?
C28 C27 C25 114.1(3) . . ?
C28 C27 H27A 108.7 . . ?
C28 C27 H27B 108.7 . . ?
C27 C28 H28A 109.5 . . ?
C27 C28 H28B 109.5 . . ?
C27 C28 H28C 109.5 . . ?
H28A C28 H28B 109.5 . . ?
H28A C28 H28C 109.5 . . ?
H28B C28 H28C 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 C1 1.355(3) . ?
O2 C10 1.230(3) . ?
O3 C11 1.235(3) . ?
O4 H4 0.8400 . ?
O4 C16 1.356(3) . ?
N1 C7 1.394(3) . ?
N1 C10 1.418(3) . ?
N1 C19 1.464(3) . ?
N2 C11 1.410(3) . ?
N2 C12 1.396(3) . ?
N2 C24 1.466(3) . ?
C1 C2 1.391(4) . ?
C1 C6 1.390(4) . ?
C2 H2 0.9500 . ?
C2 C3 1.381(4) . ?
C3 H3 0.9500 . ?
C3 C4 1.398(4) . ?
C4 C5 1.397(4) . ?
C4 C7 1.458(4) . ?
C5 H5 0.9500 . ?
C5 C6 1.379(4) . ?
C6 H6 0.9500 . ?
C7 C8 1.378(4) . ?
C8 C9 1.418(3) . ?
C8 C11 1.445(4) . ?
C9 C10 1.447(4) . ?
C9 C12 1.375(4) . ?
C12 C13 1.461(4) . ?
C13 C14 1.395(4) . ?
C13 C18 1.397(4) . ?
C14 H14 0.9500 . ?
C14 C15 1.382(4) . ?
C15 H15 0.9500 . ?
C15 C16 1.392(4) . ?
C16 C17 1.389(4) . ?
C17 H17 0.9500 . ?
C17 C18 1.382(4) . ?
C18 H18 0.9500 . ?
C19 H19A 0.9900 . ?
C19 H19B 0.9900 . ?
C19 C20 1.528(4) . ?
C20 H20 1.0000 . ?
C20 C21 1.520(4) . ?
C20 C22 1.532(4) . ?
C21 H21A 0.9800 . ?
C21 H21B 0.9800 . ?
C21 H21C 0.9800 . ?
C22 H22A 0.9900 . ?
C22 H22B 0.9900 . ?
C22 C23 1.517(5) . ?
C23 H23A 0.9800 . ?
C23 H23B 0.9800 . ?
C23 H23C 0.9800 . ?
C24 H24A 0.9900 . ?
C24 H24B 0.9900 . ?
C24 C25 1.530(4) . ?
C25 H25 1.0000 . ?
C25 C26 1.525(4) . ?
C25 C27 1.520(5) . ?
C26 H26A 0.9800 . ?
C26 H26B 0.9800 . ?
C26 H26C 0.9800 . ?
C27 H27A 0.9900 . ?
C27 H27B 0.9900 . ?
C27 C28 1.510(5) . ?
C28 H28A 0.9800 . ?
C28 H28B 0.9800 . ?
C28 H28C 0.9800 . ?
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
3.0001 2.9988 3.9980 -0.0443 0.0847 -0.9172
-3.0001 -2.9988 -3.9980 0.0443 -0.0847 0.9172
2.9991 -4.9999 2.0023 0.0428 1.0407 0.1773
-2.9991 4.9999 -2.0023 -0.0428 -1.0407 -0.1773
-7.0054 2.0003 5.0037 -0.9162 -0.5357 0.0044
7.0054 -2.0003 -5.0037 0.9162 0.5357 -0.0044
