#------------------------------------------------------------------------------
#$Date: 2023-11-06 08:38:47 +0200 (Mon, 06 Nov 2023) $
#$Revision: 287291 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/56/99/1569980.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_1569980
loop_
_publ_author_name
'Qiu, Qianfeng'
'Qi, Qingkai'
'Usuba, Junichi'
'Lee, Karina'
'Aprahamian, Ivan'
'Han, Grace G. D.'
_publ_section_title
;
 Visible light activated energy storage in solid-state Azo-BF₂
 switches.
;
_journal_issue                   41
_journal_name_full               'Chemical science'
_journal_page_first              11359
_journal_page_last               11364
_journal_paper_doi               10.1039/d3sc03465h
_journal_volume                  14
_journal_year                    2023
_chemical_formula_moiety         'C29 H35 B F2 N4 O'
_chemical_formula_sum            'C29 H35 B F2 N4 O'
_chemical_formula_weight         504.42
_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   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2023-04-17
_audit_creation_method
;
Olex2 1.5
(compiled 2023.03.06 svn.rbb2c1857 for OlexSys, GUI svn.r6748)
;
_audit_update_record
;
2023-04-20 deposited with the CCDC.	2023-09-18 downloaded from the CCDC.
;
_cell_angle_alpha                98.410(2)
_cell_angle_beta                 102.690(2)
_cell_angle_gamma                108.100(2)
_cell_formula_units_Z            2
_cell_length_a                   7.9249(2)
_cell_length_b                   11.3974(3)
_cell_length_c                   16.0639(4)
_cell_measurement_reflns_used    15549
_cell_measurement_temperature    100.0(4)
_cell_measurement_theta_max      78.9300
_cell_measurement_theta_min      2.8790
_cell_volume                     1308.96(6)
_computing_cell_refinement       'CrysAlisPro 1.171.42.89a (Rigaku OD, 2023)'
_computing_data_collection       'CrysAlisPro 1.171.42.89a (Rigaku OD, 2023)'
_computing_data_reduction        'CrysAlisPro 1.171.42.89a (Rigaku OD, 2023)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT  (Sheldrick, 2015)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.0(4)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.961
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -16.00  10.00   0.50    2.24    --   10.00  84.00 163.38   52
  2  ω     -7.00  19.00   0.50    2.24    --   14.00  74.00-120.83   52
  3  ω      0.00  26.00   0.50    2.24    --   18.00  66.00 138.19   52
  4  ω      7.00  37.00   0.50    2.24    --   22.00  58.00 -71.02   60
  5  ω      5.00  31.00   0.50    2.24    --   22.00  62.00-123.04   52
  6  ω     12.00  42.00   0.50    2.24    --   26.00  55.00  10.62   60
  7  ω     11.00  37.00   0.50    2.24    --   26.00  58.00 -27.66   52
  8  ω     16.00  44.00   0.50    2.24    --   30.00  54.00 -91.40   56
  9  ω     16.00  42.00   0.50    2.24    --   30.00  55.00 -16.21   52
 10  ω     16.00  42.00   0.50    2.24    --   30.00  55.00 120.43   52
 11  ω     20.00  46.00   0.50    2.24    --   34.00  53.00  61.36   52
 12  ω     20.00  48.00   0.50    2.24    --   34.00  52.00  91.00   56
 13  ω     24.00  50.00   0.50    2.24    --   38.00  51.00 175.31   52
 14  ω     25.00  53.00   0.50    2.24    --   38.00  50.00 157.61   56
 15  ω    -80.00  -4.00   0.50    2.24    --  -46.85 111.00  64.00  152
 16  ω     26.00  84.00   0.50    2.24    --   46.85-111.00 -29.00  116
 17  ω   -118.00 -34.00   0.50    2.24    --  -46.85 -45.00-157.47  168
 18  ω    -82.00 -15.00   0.50    2.24    --  -46.85 125.00-180.00  134
 19  ω     36.00  93.00   0.50    2.24    --   46.85-125.00-120.00  114
 20  ω     36.00  93.00   0.50    2.24    --   46.85-125.00 -60.00  114
 21  ω   -121.00 -37.00   0.50    2.24    --  -50.00 -46.00  18.51  168
 22  ω   -122.00 -37.00   0.50    2.24    --  -50.00 -45.00 103.58  170
 23  ω   -130.00 -45.00   0.50    2.24    --  -58.00 -42.00  64.91  170
 24  ω   -134.00 -49.00   0.50    2.24    --  -62.00 -47.00 177.67  170
 25  ω   -138.00 -53.00   0.50    2.24    --  -66.00 -47.00 -64.90  170
 26  ω   -138.00 -53.00   0.50    2.24    --  -66.00 -47.00  -0.74  170
 27  ω   -138.00 -52.00   0.50    2.24    --  -66.00 -44.00-157.69  172
 28  ω   -138.00 -53.00   0.50    2.24    --  -66.00 -45.00 -43.00  170
 29  ω   -142.00 -57.00   0.50    2.24    --  -70.00 -46.00  41.46  170
 30  ω   -142.00 -57.00   0.50    2.24    --  -70.00 -47.00-101.90  170
 31  ω   -142.00 -57.00   0.50    2.24    --  -70.00 -47.00 -16.68  170
 32  ω   -142.00 -57.00   0.50    2.24    --  -70.00 -47.00  28.39  170
 33  ω   -142.00 -57.00   0.50    2.24    --  -70.00 -47.00 164.05  170
 34  ω   -142.00 -57.00   0.50    2.24    --  -70.00 -46.00 115.42  170
 35  ω   -146.00 -61.00   0.50    2.24    --  -74.00 -45.00  74.34  170
 36  ω   -146.00 -60.00   0.50    2.24    --  -74.00 -44.00  97.44  172
 37  ω   -146.00 -61.00   0.50    2.24    --  -74.00 -45.00 -80.64  170
 38  ω   -145.00 -61.00   0.50    2.24    --  -74.00 -46.00 -50.04  168
 39  ω   -146.00 -61.00   0.50    2.24    --  -74.00 -45.00-113.88  170
 40  ω    -95.00 -62.00   0.50    2.24    --  -74.00 -41.00 132.81   66
 41  ω    -94.00 -69.00   0.50    8.95    --  -82.00 -46.00  49.22   50
 42  ω    -96.00 -69.00   0.50    8.95    --  -82.00 -46.00-135.39   54
 43  ω    -95.00 -69.00   0.50    8.95    --  -82.00 -45.00-167.58   52
 44  ω   -160.00 -83.00   0.50    8.95    --  -91.75-111.00 -29.00  154
 45  ω    -80.00 -23.00   0.50    8.95    --  -91.75 111.00  64.00  114
 46  ω   -116.00 -79.00   0.50    8.95    --  -91.75 -46.00 145.34   74
 47  ω   -163.00-132.00   0.50    8.95    --  -91.75 -45.00 120.00   62
 48  ω   -162.00-110.00   0.50    8.95    --  -91.75 -45.00 -90.00  104
 49  ω   -124.00 -80.00   0.50    8.95    --  -91.75 -46.00  79.33   88
 50  ω   -107.00 -81.00   0.50    8.95    --  -91.75 -45.00-146.14   52
 51  ω   -104.00 -79.00   0.50    8.95    --  -91.75 -45.00  46.21   50
 52  ω   -152.00-127.00   0.50    8.95    --  -91.75 -45.00  46.21   50
 53  ω   -105.00 -79.00   0.50    8.95    --  -91.75 -46.00-112.72   52
 54  ω   -112.00 -80.00   0.50    8.95    --  -91.75 -45.00 -30.00   64
 55  ω   -114.00 -79.00   0.50    8.95    --  -91.75 -46.00 173.35   70
 56  ω   -147.00-120.00   0.50    8.95    --  -91.75 -46.00 173.35   54
 57  ω   -111.00 -82.00   0.50    8.95    --  -91.75 -45.00 -47.59   58
 58  ω   -108.00 -82.00   0.50    8.95    --  -91.75 -47.00 -69.58   52
 59  ω   -107.00 -79.00   0.50    8.95    --  -91.75 -45.00   0.00   56
 60  ω   -104.00 -79.00   0.50    8.95    --  -91.75 -45.00 120.00   50
 61  ω   -163.00-127.00   0.50    8.95    --  -91.75 -45.00   0.00   72
 62  ω   -121.00 -84.00   0.50    8.95    --  -91.75 -47.00 109.49   74
 63  ω   -106.00 -79.00   0.50    8.95    --  -91.75 -45.00  30.00   54
 64  ω   -129.00 -86.00   0.50    8.95    --  -91.75 -47.00-163.54   86
 65  ω   -111.00 -79.00   0.50    8.95    --  -91.75 -46.00 -10.77   64
 66  ω   -105.00 -79.00   0.50    8.95    --  -91.75 -45.00 -90.00   52
 67  ω   -110.00 -83.00   0.50    8.95    --  -91.75 -47.00  20.27   54
 68  ω    105.00 178.00   0.50    8.95    --  113.25 111.00  64.00  146
 69  ω     45.00 106.00   0.50    8.95    --  113.25-111.00 -29.00  122
 70  ω    108.00 157.00   0.50    8.95    --  113.25 125.00 -60.00   98
 71  ω     53.00 107.00   0.50    8.95    --  113.25-125.00 -60.00  108
 72  ω    150.00 176.00   0.50    8.95    --  113.25  45.00-150.00   52
 73  ω    102.00 138.00   0.50    8.95    --  113.25  45.00-120.00   72
 74  ω    111.00 178.00   0.50    8.95    --  113.25  77.00   0.00  134
 75  ω    104.00 146.00   0.50    8.95    --  113.25  45.00-150.00   84
 76  ω    150.00 177.00   0.50    8.95    --  113.25  61.00 -90.00   54
 77  ω    107.00 136.00   0.50    8.95    --  113.25  61.00 -90.00   58
 78  ω    101.00 127.00   0.50    8.95    --  113.25  45.00-180.00   52
 79  ω     83.00 108.00   0.50    8.95    --  113.25-125.00  90.00   50
 80  ω     76.00 105.00   0.50    8.95    --  113.25-105.00 120.40   58
 81  ω    138.00 177.00   0.50    8.95    --  113.25  45.00  90.00   78
 82  ω     42.00  80.00   0.50    8.95    --  113.25 -77.00-150.00   76
 83  ω    148.00 178.00   0.50    8.95    --  113.25  61.00-180.00   60
 84  ω    101.00 136.00   0.50    8.95    --  113.25  45.00  90.00   70
 85  ω    107.00 144.00   0.50    8.95    --  113.25  61.00-180.00   74
 86  ω     44.00  89.00   0.50    8.95    --  113.25 -77.00-120.00   90
 87  ω     45.00 103.00   0.50    8.95    --  113.25-125.00 120.00  116
 88  ω     78.00 103.00   0.50    8.95    --  113.25 -94.00-180.00   50
 89  ω     54.00  79.00   0.50    8.95    --  113.25-125.00  90.00   50
 90  ω    101.00 159.00   0.50    8.95    --  113.25  45.00 120.00  116
 91  ω     79.00 104.00   0.50    8.95    --  113.25 -94.00 150.00   50
 92  ω     43.00  68.00   0.50    8.95    --  113.25 -94.00 150.00   50
 93  ω     76.00 102.00   0.50    8.95    --  113.25 -94.00-150.00   52
 94  ω     44.00  89.00   0.50    8.95    --  113.25 -77.00   0.00   90
 95  ω    108.00 171.00   0.50    8.95    --  113.25  61.00 -30.00  126
 96  ω     42.00  68.00   0.50    8.95    --  113.25 -94.00-150.00   52
 97  ω    102.00 129.00   0.50    8.95    --  113.25  45.00 -30.00   54
 98  ω     79.00 104.00   0.50    8.95    --  113.25 -94.00 120.00   50
 99  ω     42.00  74.00   0.50    8.95    --  113.25 -94.00-180.00   64
100  ω    109.00 159.00   0.50    8.95    --  113.25  45.00 -60.00  100
101  ω    106.00 176.00   0.50    8.95    --  113.25  61.00-120.00  140
102  ω     42.00  67.00   0.50    8.95    --  113.25 -77.00  60.00   50
103  ω    134.00 160.00   0.50    8.95    --  113.25  45.00 -90.00   52
104  ω    101.00 128.00   0.50    8.95    --  113.25  45.00 -90.00   54
105  ω     42.00  67.00   0.50    8.95    --  113.25 -94.00 120.00   50
106  ω    148.00 178.00   0.50    8.95    --  113.25  77.00 150.00   60
107  ω    116.00 129.00   0.50    8.95    --  113.25  77.00 150.00   26
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0442449000
_diffrn_orient_matrix_UB_12      -0.0178949000
_diffrn_orient_matrix_UB_13      0.0945681000
_diffrn_orient_matrix_UB_21      -0.0680077000
_diffrn_orient_matrix_UB_22      0.1076110000
_diffrn_orient_matrix_UB_23      0.0295837000
_diffrn_orient_matrix_UB_31      -0.1971203000
_diffrn_orient_matrix_UB_32      -0.0972880000
_diffrn_orient_matrix_UB_33      -0.0197884000
_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  0.0514
_diffrn_reflns_av_unetI/netI     0.0281
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.961
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            43444
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.961
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         80.287
_diffrn_reflns_theta_min         2.898
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_current           1
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_diffrn_source_voltage           50
_exptl_absorpt_coefficient_mu    0.713
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.663
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.42.89a (Rigaku Oxford Diffraction, 2023)
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            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.280
_exptl_crystal_description       needle
_exptl_crystal_F_000             536
_exptl_crystal_recrystallization_method 'used as recieved'
_exptl_crystal_size_max          0.333
_exptl_crystal_size_mid          0.038
_exptl_crystal_size_min          0.015
_refine_diff_density_max         1.595
_refine_diff_density_min         -0.495
_refine_diff_density_rms         0.074
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.118
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     335
_refine_ls_number_reflns         5503
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.118
_refine_ls_R_factor_all          0.0999
_refine_ls_R_factor_gt           0.0902
_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)+(0.1070P)²+1.9777P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2406
_refine_ls_wR_factor_ref         0.2478
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4761
_reflns_number_total             5503
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d3sc03465h2.cif
_cod_data_source_block           ia423d
_cod_depositor_comments
'Adding full bibliography for 1569977--1569980.cif.'
_cod_database_code               1569980
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         C29H35BF2N4O
_chemical_oxdiff_usercomment     AzoBF2-12C
_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   0.989
_shelx_estimated_absorpt_t_min   0.797
_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.a Secondary CH2 refined with riding coordinates:
 C18(H18A,H18B), C19(H19A,H19B), C20(H20A,H20B), C21(H21A,H21B), C22(H22A,
 H22B), C23(H23A,H23B), C24(H24A,H24B), C25(H25A,H25B), C26(H26A,H26B),
 C27(H27A,H27B), C28(H28A,H28B)
2.b Aromatic/amide H refined with riding coordinates:
 C3(H3), C4(H4), C6(H6), C7(H7), C8(H8), C9(H9), C13(H13), C14(H14), C16(H16),
 C17(H17)
2.c Idealised Me refined as rotating group:
 C29(H29A,H29B,H29C)
;
_olex2_diffrn_ambient_temperature_device 'Oxford Cryosystems'
_olex2_exptl_crystal_mounting_method
'The crystal was mounted on a nylon loop with paratone oil'
_olex2_submission_original_sample_id AzoBF2-12C
_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 1.682
_oxdiff_exptl_absorpt_empirical_full_min 0.605
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
F1 F 1.5033(3) 0.73492(17) 0.75430(12) 0.0413(5) Uani 1 1 d . . . . .
F2 F 1.4772(3) 0.81655(17) 0.88743(12) 0.0408(5) Uani 1 1 d . . . . .
O1 O 0.6200(3) 0.50831(19) 0.67228(15) 0.0351(5) Uani 1 1 d . . . . .
N1 N 1.4661(4) 0.5946(3) 0.85922(19) 0.0438(7) Uani 1 1 d . . . . .
N2 N 1.3118(5) 0.5098(3) 0.84597(19) 0.0459(7) Uani 1 1 d . . . . .
N3 N 1.7489(4) 0.7648(2) 0.88194(16) 0.0330(6) Uani 1 1 d . . . . .
N4 N 1.6074(4) 0.3557(3) 0.9425(2) 0.0479(7) Uani 1 1 d . . . . .
C1 C 1.6163(4) 0.5644(3) 0.9004(2) 0.0353(7) Uani 1 1 d . . . . .
C2 C 1.7810(4) 0.6680(3) 0.91325(19) 0.0329(6) Uani 1 1 d . . . . .
C3 C 1.9642(5) 0.6771(3) 0.9537(2) 0.0373(7) Uani 1 1 d . . . . .
H3 H 1.986403 0.609175 0.976462 0.045 Uiso 1 1 calc R U . . .
C4 C 2.1061(5) 0.7830(3) 0.9593(2) 0.0380(7) Uani 1 1 d . . . . .
H4 H 2.229004 0.789117 0.985936 0.046 Uiso 1 1 calc R U . . .
C5 C 2.0752(4) 0.8866(3) 0.92604(19) 0.0362(7) Uani 1 1 d . . . . .
C6 C 2.2171(5) 0.9993(3) 0.9321(2) 0.0400(7) Uani 1 1 d . . . . .
H6 H 2.341494 1.008670 0.958737 0.048 Uiso 1 1 calc R U . . .
C7 C 2.1812(5) 1.0966(3) 0.9007(2) 0.0424(8) Uani 1 1 d . . . . .
H7 H 2.279462 1.173210 0.906005 0.051 Uiso 1 1 calc R U . . .
C8 C 1.9981(5) 1.0823(3) 0.8605(2) 0.0413(8) Uani 1 1 d . . . . .
H8 H 1.973472 1.149469 0.837654 0.050 Uiso 1 1 calc R U . . .
C9 C 1.8536(4) 0.9738(3) 0.8533(2) 0.0354(7) Uani 1 1 d . . . . .
H9 H 1.730149 0.965863 0.826185 0.043 Uiso 1 1 calc R U . . .
C10 C 1.8906(4) 0.8737(3) 0.88687(19) 0.0334(6) Uani 1 1 d . . . . .
C11 C 1.6099(4) 0.4487(3) 0.9243(2) 0.0378(7) Uani 1 1 d . . . . .
C12 C 1.1464(5) 0.5281(3) 0.8017(2) 0.0402(8) Uani 1 1 d . . . . .
C13 C 1.1161(4) 0.6248(3) 0.7611(2) 0.0394(7) Uani 1 1 d . . . . .
H13 H 1.218145 0.696771 0.762471 0.047 Uiso 1 1 calc R U . . .
C14 C 0.9381(4) 0.6144(3) 0.7195(2) 0.0350(7) Uani 1 1 d . . . . .
H14 H 0.918263 0.679727 0.692571 0.042 Uiso 1 1 calc R U . . .
C15 C 0.7880(4) 0.5090(3) 0.7166(2) 0.0325(6) Uani 1 1 d . . . . .
C16 C 0.8171(5) 0.4151(3) 0.7579(2) 0.0389(7) Uani 1 1 d . . . . .
H16 H 0.714835 0.343785 0.757386 0.047 Uiso 1 1 calc R U . . .
C17 C 0.9939(5) 0.4257(3) 0.7995(2) 0.0420(8) Uani 1 1 d . . . . .
H17 H 1.012131 0.360937 0.827476 0.050 Uiso 1 1 calc R U . . .
C18 C 0.4600(4) 0.3996(3) 0.6619(2) 0.0328(6) Uani 1 1 d . . . . .
H18A H 0.441919 0.389211 0.719833 0.039 Uiso 1 1 calc R U . . .
H18B H 0.474152 0.322052 0.632486 0.039 Uiso 1 1 calc R U . . .
C19 C 0.2972(4) 0.4217(3) 0.6067(2) 0.0331(6) Uani 1 1 d . . . . .
H19A H 0.317516 0.431454 0.549085 0.040 Uiso 1 1 calc R U . . .
H19B H 0.288683 0.501534 0.635887 0.040 Uiso 1 1 calc R U . . .
C20 C 0.1157(4) 0.3132(3) 0.5925(2) 0.0316(6) Uani 1 1 d . . . . .
H20A H 0.123825 0.233677 0.562464 0.038 Uiso 1 1 calc R U . . .
H20B H 0.097058 0.302350 0.650267 0.038 Uiso 1 1 calc R U . . .
C21 C -0.0507(4) 0.3347(3) 0.5384(2) 0.0325(6) Uani 1 1 d . . . . .
H21A H -0.032481 0.344915 0.480492 0.039 Uiso 1 1 calc R U . . .
H21B H -0.058226 0.414601 0.568223 0.039 Uiso 1 1 calc R U . . .
C22 C -0.2327(4) 0.2268(3) 0.52466(19) 0.0312(6) Uani 1 1 d . . . . .
H22A H -0.252596 0.218300 0.582539 0.037 Uiso 1 1 calc R U . . .
H22B H -0.223810 0.146595 0.496417 0.037 Uiso 1 1 calc R U . . .
C23 C -0.3990(4) 0.2465(3) 0.46834(19) 0.0325(6) Uani 1 1 d . . . . .
H23A H -0.377594 0.257444 0.411060 0.039 Uiso 1 1 calc R U . . .
H23B H -0.410172 0.325361 0.497439 0.039 Uiso 1 1 calc R U . . .
C24 C -0.5801(4) 0.1363(3) 0.45263(19) 0.0327(6) Uani 1 1 d . . . . .
H24A H -0.568797 0.057646 0.423202 0.039 Uiso 1 1 calc R U . . .
H24B H -0.600384 0.124883 0.510033 0.039 Uiso 1 1 calc R U . . .
C25 C -0.7483(4) 0.1547(3) 0.39709(19) 0.0320(6) Uani 1 1 d . . . . .
H25A H -0.763009 0.231413 0.427543 0.038 Uiso 1 1 calc R U . . .
H25B H -0.726606 0.169176 0.340427 0.038 Uiso 1 1 calc R U . . .
C26 C -0.9262(4) 0.0418(3) 0.3794(2) 0.0329(6) Uani 1 1 d . . . . .
H26A H -0.912980 -0.033648 0.346311 0.039 Uiso 1 1 calc R U . . .
H26B H -0.943088 0.024496 0.436228 0.039 Uiso 1 1 calc R U . . .
C27 C -1.0991(4) 0.0593(3) 0.32831(19) 0.0316(6) Uani 1 1 d . . . . .
H27A H -1.114838 0.133222 0.362067 0.038 Uiso 1 1 calc R U . . .
H27B H -1.081596 0.078596 0.272011 0.038 Uiso 1 1 calc R U . . .
C28 C -1.2743(4) -0.0556(3) 0.3094(2) 0.0352(7) Uani 1 1 d . . . . .
H28A H -1.291786 -0.075386 0.365603 0.042 Uiso 1 1 calc R U . . .
H28B H -1.259414 -0.129486 0.275125 0.042 Uiso 1 1 calc R U . . .
C29 C -1.4463(4) -0.0363(3) 0.2588(2) 0.0397(7) Uani 1 1 d . . . . .
H29A H -1.432123 -0.019963 0.202066 0.060 Uiso 1 1 calc R U . . .
H29B H -1.462599 0.036324 0.292565 0.060 Uiso 1 1 calc R U . . .
H29C H -1.554963 -0.112669 0.249337 0.060 Uiso 1 1 calc R U . . .
B1 B 1.5424(5) 0.7378(3) 0.8417(2) 0.0374(8) 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'
B B 0.0090 0.0039 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0727 0.0534 '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 0.0061
0 1 0 0.0317
0 0 -1 0.0077
0 0 1 0.0077
-1 0 0 0.1602
1 0 0 0.1354
-4 6 1 0.1552
0 1 -1 0.0252
0 -1 1 0.0064
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
C15 O1 C18 118.4(2) . . ?
N2 N1 C1 114.4(3) . . ?
N2 N1 B1 136.4(3) . . ?
C1 N1 B1 109.2(3) . . ?
N1 N2 C12 119.7(3) . . ?
C2 N3 C10 121.5(3) . . ?
C2 N3 B1 112.9(3) . . ?
C10 N3 B1 125.6(3) . . ?
N1 C1 C2 108.9(3) . . ?
N1 C1 C11 126.8(3) . . ?
C2 C1 C11 124.3(3) . . ?
N3 C2 C1 112.3(3) . . ?
N3 C2 C3 120.6(3) . . ?
C1 C2 C3 127.1(3) . . ?
C2 C3 H3 120.4 . . ?
C4 C3 C2 119.2(3) . . ?
C4 C3 H3 120.4 . . ?
C3 C4 H4 119.4 . . ?
C3 C4 C5 121.2(3) . . ?
C5 C4 H4 119.4 . . ?
C6 C5 C4 123.4(3) . . ?
C6 C5 C10 118.9(3) . . ?
C10 C5 C4 117.7(3) . . ?
C5 C6 H6 119.3 . . ?
C7 C6 C5 121.4(3) . . ?
C7 C6 H6 119.3 . . ?
C6 C7 H7 120.4 . . ?
C6 C7 C8 119.3(3) . . ?
C8 C7 H7 120.4 . . ?
C7 C8 H8 119.2 . . ?
C9 C8 C7 121.5(3) . . ?
C9 C8 H8 119.2 . . ?
C8 C9 H9 120.4 . . ?
C8 C9 C10 119.2(3) . . ?
C10 C9 H9 120.4 . . ?
N3 C10 C5 119.9(3) . . ?
N3 C10 C9 120.5(3) . . ?
C5 C10 C9 119.6(3) . . ?
N4 C11 C1 178.5(4) . . ?
C13 C12 N2 132.7(3) . . ?
C17 C12 N2 109.1(3) . . ?
C17 C12 C13 118.2(3) . . ?
C12 C13 H13 120.0 . . ?
C14 C13 C12 120.0(3) . . ?
C14 C13 H13 120.0 . . ?
C13 C14 H14 119.8 . . ?
C13 C14 C15 120.4(3) . . ?
C15 C14 H14 119.8 . . ?
O1 C15 C14 115.0(3) . . ?
O1 C15 C16 125.3(3) . . ?
C16 C15 C14 119.7(3) . . ?
C15 C16 H16 120.1 . . ?
C17 C16 C15 119.8(3) . . ?
C17 C16 H16 120.1 . . ?
C12 C17 H17 119.1 . . ?
C16 C17 C12 121.8(3) . . ?
C16 C17 H17 119.1 . . ?
O1 C18 H18A 110.3 . . ?
O1 C18 H18B 110.3 . . ?
O1 C18 C19 106.9(2) . . ?
H18A C18 H18B 108.6 . . ?
C19 C18 H18A 110.3 . . ?
C19 C18 H18B 110.3 . . ?
C18 C19 H19A 109.2 . . ?
C18 C19 H19B 109.2 . . ?
C18 C19 C20 112.2(2) . . ?
H19A C19 H19B 107.9 . . ?
C20 C19 H19A 109.2 . . ?
C20 C19 H19B 109.2 . . ?
C19 C20 H20A 109.0 . . ?
C19 C20 H20B 109.0 . . ?
H20A C20 H20B 107.8 . . ?
C21 C20 C19 113.0(2) . . ?
C21 C20 H20A 109.0 . . ?
C21 C20 H20B 109.0 . . ?
C20 C21 H21A 109.0 . . ?
C20 C21 H21B 109.0 . . ?
C20 C21 C22 113.1(2) . . ?
H21A C21 H21B 107.8 . . ?
C22 C21 H21A 109.0 . . ?
C22 C21 H21B 109.0 . . ?
C21 C22 H22A 108.9 . . ?
C21 C22 H22B 108.9 . . ?
C21 C22 C23 113.2(2) . . ?
H22A C22 H22B 107.7 . . ?
C23 C22 H22A 108.9 . . ?
C23 C22 H22B 108.9 . . ?
C22 C23 H23A 109.0 . . ?
C22 C23 H23B 109.0 . . ?
C22 C23 C24 113.0(2) . . ?
H23A C23 H23B 107.8 . . ?
C24 C23 H23A 109.0 . . ?
C24 C23 H23B 109.0 . . ?
C23 C24 H24A 108.8 . . ?
C23 C24 H24B 108.8 . . ?
H24A C24 H24B 107.7 . . ?
C25 C24 C23 113.8(2) . . ?
C25 C24 H24A 108.8 . . ?
C25 C24 H24B 108.8 . . ?
C24 C25 H25A 109.0 . . ?
C24 C25 H25B 109.0 . . ?
H25A C25 H25B 107.8 . . ?
C26 C25 C24 112.9(2) . . ?
C26 C25 H25A 109.0 . . ?
C26 C25 H25B 109.0 . . ?
C25 C26 H26A 108.6 . . ?
C25 C26 H26B 108.6 . . ?
H26A C26 H26B 107.6 . . ?
C27 C26 C25 114.6(2) . . ?
C27 C26 H26A 108.6 . . ?
C27 C26 H26B 108.6 . . ?
C26 C27 H27A 108.8 . . ?
C26 C27 H27B 108.8 . . ?
H27A C27 H27B 107.7 . . ?
C28 C27 C26 113.7(2) . . ?
C28 C27 H27A 108.8 . . ?
C28 C27 H27B 108.8 . . ?
C27 C28 H28A 109.0 . . ?
C27 C28 H28B 109.0 . . ?
C27 C28 C29 113.1(3) . . ?
H28A C28 H28B 107.8 . . ?
C29 C28 H28A 109.0 . . ?
C29 C28 H28B 109.0 . . ?
C28 C29 H29A 109.5 . . ?
C28 C29 H29B 109.5 . . ?
C28 C29 H29C 109.5 . . ?
H29A C29 H29B 109.5 . . ?
H29A C29 H29C 109.5 . . ?
H29B C29 H29C 109.5 . . ?
F1 B1 F2 113.4(3) . . ?
F1 B1 N1 111.4(3) . . ?
F1 B1 N3 111.4(3) . . ?
F2 B1 N1 110.0(3) . . ?
F2 B1 N3 112.7(3) . . ?
N3 B1 N1 96.7(3) . . ?
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
F1 B1 1.363(4) . ?
F2 B1 1.369(4) . ?
O1 C15 1.362(4) . ?
O1 C18 1.429(3) . ?
N1 N2 1.251(4) . ?
N1 C1 1.395(4) . ?
N1 B1 1.645(5) . ?
N2 C12 1.440(4) . ?
N3 C2 1.347(4) . ?
N3 C10 1.369(4) . ?
N3 B1 1.534(5) . ?
N4 C11 1.135(4) . ?
C1 C2 1.412(5) . ?
C1 C11 1.416(5) . ?
C2 C3 1.419(4) . ?
C3 H3 0.9500 . ?
C3 C4 1.345(5) . ?
C4 H4 0.9500 . ?
C4 C5 1.431(5) . ?
C5 C6 1.394(5) . ?
C5 C10 1.412(4) . ?
C6 H6 0.9500 . ?
C6 C7 1.364(5) . ?
C7 H7 0.9500 . ?
C7 C8 1.400(5) . ?
C8 H8 0.9500 . ?
C8 C9 1.369(5) . ?
C9 H9 0.9500 . ?
C9 C10 1.412(4) . ?
C12 C13 1.415(5) . ?
C12 C17 1.384(5) . ?
C13 H13 0.9500 . ?
C13 C14 1.382(4) . ?
C14 H14 0.9500 . ?
C14 C15 1.390(4) . ?
C15 C16 1.390(5) . ?
C16 H16 0.9500 . ?
C16 C17 1.373(5) . ?
C17 H17 0.9500 . ?
C18 H18A 0.9900 . ?
C18 H18B 0.9900 . ?
C18 C19 1.510(4) . ?
C19 H19A 0.9900 . ?
C19 H19B 0.9900 . ?
C19 C20 1.523(4) . ?
C20 H20A 0.9900 . ?
C20 H20B 0.9900 . ?
C20 C21 1.521(4) . ?
C21 H21A 0.9900 . ?
C21 H21B 0.9900 . ?
C21 C22 1.523(4) . ?
C22 H22A 0.9900 . ?
C22 H22B 0.9900 . ?
C22 C23 1.524(4) . ?
C23 H23A 0.9900 . ?
C23 H23B 0.9900 . ?
C23 C24 1.526(4) . ?
C24 H24A 0.9900 . ?
C24 H24B 0.9900 . ?
C24 C25 1.524(4) . ?
C25 H25A 0.9900 . ?
C25 H25B 0.9900 . ?
C25 C26 1.522(4) . ?
C26 H26A 0.9900 . ?
C26 H26B 0.9900 . ?
C26 C27 1.521(4) . ?
C27 H27A 0.9900 . ?
C27 H27B 0.9900 . ?
C27 C28 1.518(4) . ?
C28 H28A 0.9900 . ?
C28 H28B 0.9900 . ?
C28 C29 1.523(4) . ?
C29 H29A 0.9800 . ?
C29 H29B 0.9800 . ?
C29 H29C 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
O1 C15 C16 C17 178.9(3) . . . . ?
O1 C18 C19 C20 -178.6(2) . . . . ?
N1 N2 C12 C13 5.2(5) . . . . ?
N1 N2 C12 C17 -176.4(3) . . . . ?
N1 C1 C2 N3 -0.7(3) . . . . ?
N1 C1 C2 C3 179.3(3) . . . . ?
N2 N1 C1 C2 -178.8(3) . . . . ?
N2 N1 C1 C11 2.7(4) . . . . ?
N2 N1 B1 F1 -64.9(5) . . . . ?
N2 N1 B1 F2 61.8(5) . . . . ?
N2 N1 B1 N3 178.9(3) . . . . ?
N2 C12 C13 C14 177.1(3) . . . . ?
N2 C12 C17 C16 -177.3(3) . . . . ?
N3 C2 C3 C4 -0.9(4) . . . . ?
C1 N1 N2 C12 -178.3(3) . . . . ?
C1 N1 B1 F1 116.1(3) . . . . ?
C1 N1 B1 F2 -117.2(3) . . . . ?
C1 N1 B1 N3 -0.1(3) . . . . ?
C1 C2 C3 C4 179.1(3) . . . . ?
C2 N3 C10 C5 -0.5(4) . . . . ?
C2 N3 C10 C9 179.8(3) . . . . ?
C2 N3 B1 F1 -116.5(3) . . . . ?
C2 N3 B1 F2 114.7(3) . . . . ?
C2 N3 B1 N1 -0.3(3) . . . . ?
C2 C3 C4 C5 0.5(4) . . . . ?
C3 C4 C5 C6 178.5(3) . . . . ?
C3 C4 C5 C10 -0.1(4) . . . . ?
C4 C5 C6 C7 -178.9(3) . . . . ?
C4 C5 C10 N3 0.1(4) . . . . ?
C4 C5 C10 C9 179.8(3) . . . . ?
C5 C6 C7 C8 -0.8(5) . . . . ?
C6 C5 C10 N3 -178.6(3) . . . . ?
C6 C5 C10 C9 1.2(4) . . . . ?
C6 C7 C8 C9 1.2(5) . . . . ?
C7 C8 C9 C10 -0.4(5) . . . . ?
C8 C9 C10 N3 179.0(3) . . . . ?
C8 C9 C10 C5 -0.8(4) . . . . ?
C10 N3 C2 C1 -179.1(2) . . . . ?
C10 N3 C2 C3 0.9(4) . . . . ?
C10 N3 B1 F1 63.3(4) . . . . ?
C10 N3 B1 F2 -65.5(4) . . . . ?
C10 N3 B1 N1 179.5(2) . . . . ?
C10 C5 C6 C7 -0.4(4) . . . . ?
C11 C1 C2 N3 177.8(3) . . . . ?
C11 C1 C2 C3 -2.2(5) . . . . ?
C12 C13 C14 C15 -0.4(5) . . . . ?
C13 C12 C17 C16 1.2(5) . . . . ?
C13 C14 C15 O1 -178.7(3) . . . . ?
C13 C14 C15 C16 1.6(5) . . . . ?
C14 C15 C16 C17 -1.4(5) . . . . ?
C15 O1 C18 C19 -177.0(2) . . . . ?
C15 C16 C17 C12 0.0(5) . . . . ?
C17 C12 C13 C14 -1.0(4) . . . . ?
C18 O1 C15 C14 176.3(2) . . . . ?
C18 O1 C15 C16 -4.1(4) . . . . ?
C18 C19 C20 C21 178.9(2) . . . . ?
C19 C20 C21 C22 -179.6(2) . . . . ?
C20 C21 C22 C23 -178.4(2) . . . . ?
C21 C22 C23 C24 178.4(2) . . . . ?
C22 C23 C24 C25 179.5(2) . . . . ?
C23 C24 C25 C26 177.9(2) . . . . ?
C24 C25 C26 C27 176.8(2) . . . . ?
C25 C26 C27 C28 178.5(2) . . . . ?
C26 C27 C28 C29 179.6(3) . . . . ?
B1 N1 N2 C12 2.8(5) . . . . ?
B1 N1 C1 C2 0.5(3) . . . . ?
B1 N1 C1 C11 -178.0(3) . . . . ?
B1 N3 C2 C1 0.7(3) . . . . ?
B1 N3 C2 C3 -179.3(3) . . . . ?
B1 N3 C10 C5 179.7(3) . . . . ?
B1 N3 C10 C9 0.0(4) . . . . ?
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
0.0004 -0.9993 0.0003 0.0179 -0.1076 0.0971
-0.0004 0.9993 -0.0003 -0.0179 0.1076 -0.0971
0.0010 -0.0005 -1.0018 -0.0947 -0.0298 0.0197
-0.0010 0.0005 1.0018 0.0947 0.0298 -0.0197
-1.0030 0.0006 -0.0016 -0.0445 0.0682 0.1977
1.0030 -0.0006 0.0016 0.0445 -0.0682 -0.1977
-4.3176 5.7873 1.2244 -0.1788 0.9526 0.2638
0.0006 0.9988 -1.0021 -0.1126 0.0778 -0.0775
-0.0006 -0.9988 1.0021 0.1126 -0.0778 0.0775
