#------------------------------------------------------------------------------
#$Date: 2021-10-03 22:52:08 +0300 (Sun, 03 Oct 2021) $
#$Revision: 269485 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/51/90/4519063.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_4519063
loop_
_publ_author_name
'Herraiz, Ana G.'
'Cramer, Nicolai'
_publ_section_title
;
 Cobalt(III)-Catalyzed Diastereo- and Enantioselective Three-Component
 C--H Functionalization
;
_journal_issue                   19
_journal_name_full               'ACS Catalysis'
_journal_page_first              11938
_journal_page_last               11944
_journal_paper_doi               10.1021/acscatal.1c03153
_journal_volume                  11
_journal_year                    2021
_chemical_absolute_configuration rmad
_chemical_formula_moiety         'C28 H26 N2 O2'
_chemical_formula_sum            'C28 H26 N2 O2'
_chemical_formula_weight         422.51
_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   mixed
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_audit_creation_date             2021-04-14
_audit_creation_method
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6272)
;
_cell_angle_alpha                90
_cell_angle_beta                 97.8768(8)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   8.18927(8)
_cell_length_b                   12.80314(10)
_cell_length_c                   10.83576(9)
_cell_measurement_reflns_used    14926
_cell_measurement_temperature    140.00(10)
_cell_measurement_theta_max      75.8900
_cell_measurement_theta_min      4.0820
_cell_volume                     1125.393(17)
_computing_cell_refinement       'CrysAlisPro 1.171.41.105a (Rigaku OD, 2021)'
_computing_data_collection       'CrysAlisPro 1.171.41.105a (Rigaku OD, 2021)'
_computing_data_reduction        'CrysAlisPro 1.171.41.105a (Rigaku OD, 2021)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT 2018/2 (Sheldrick, 2015)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      140.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2817
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
--------------------------------------------------------------------------
  1  ω    -83.00   3.00   1.00    1.00    --  -40.91 112.00 -57.00   86
  2  ω     18.00  84.00   1.00    1.00    --   40.91-112.00-150.00   66
  3  ω     72.00  98.00   1.00    4.00    --  112.00-112.00-150.00   26
  4  ω    132.00 158.00   1.00    4.00    --  112.00 112.00 -57.00   26
  5  ω   -114.00 -16.00   1.00    1.00    --  -40.91 -38.00   0.00   98
  6  ω    -54.00 -24.00   1.00    1.00    --  -40.91 -38.00-150.00   30
  7  ω    -48.00 -17.00   1.00    1.00    --  -40.91 -57.00-180.00   31
  8  ω   -112.00 -50.00   1.00    1.00    --  -40.91 -57.00-180.00   62
  9  ω      6.00  31.00   1.00    1.00    --   40.91  85.00 -74.74   25
 10  ω    -20.00  72.00   1.00    1.00    --   40.91 -77.00  60.00   92
 11  ω     10.00  35.00   1.00    1.00    --   42.00  74.00 136.83   25
 12  ω     12.00  38.00   1.00    1.00    --   46.00  82.00 -75.20   26
 13  ω     16.00  41.00   1.00    1.00    --   50.00  81.00 105.70   25
 14  ω     16.00  42.00   1.00    1.00    --   50.00  82.00-120.04   26
 15  ω     16.00  41.00   1.00    1.00    --   50.00  82.00 -15.02   25
 16  ω     16.00  41.00   1.00    1.00    --   50.00  82.00 160.87   25
 17  ω     82.00 109.00   1.00    1.00    --   58.00  64.00-126.38   27
 18  ω     35.00  65.00   1.00    1.00    --   58.00  64.00-126.38   30
 19  ω     95.00 134.00   1.00    1.00    --   62.00  69.00  54.74   39
 20  ω     31.00  58.00   1.00    1.00    --   62.00  69.00  54.74   27
 21  ω     35.00  62.00   1.00    1.00    --   66.00  71.00  82.12   27
 22  ω    101.00 127.00   1.00    1.00    --   66.00  71.00  82.12   26
 23  ω     37.00  62.00   1.00    1.00    --   66.00  70.00-174.39   25
 24  ω     40.00  66.00   1.00    1.00    --   70.00  66.00  59.28   26
 25  ω     39.00  89.00   1.00    1.00    --   70.00  71.00 145.90   50
 26  ω     39.00  70.00   1.00    1.00    --   70.00  70.00 104.12   31
 27  ω     40.00  91.00   1.00    1.00    --   70.00  70.00 -46.41   51
 28  ω     43.00  68.00   1.00    1.00    --   74.00  70.00-104.86   25
 29  ω    115.00 146.00   1.00    1.00    --   74.00  69.00 -75.46   31
 30  ω    112.00 148.00   1.00    1.00    --   74.00  71.00  -6.90   36
 31  ω     43.00  69.00   1.00    1.00    --   74.00  69.00 -75.46   26
 32  ω     43.00  95.00   1.00    1.00    --   74.00  71.00  -6.90   52
 33  ω     52.00  86.00   1.00    4.00    --   82.00  68.00 169.46   34
 34  ω     65.00 102.00   1.00    4.00    --   90.00  52.00-144.19   37
 35  ω     65.00 155.00   1.00    4.00    --   94.00  68.00 -74.97   90
 36  ω     72.00  99.00   1.00    4.00    --  102.00  68.00  16.95   27
 37  ω     48.00 107.00   1.00    4.00    --  112.00 -94.00 -60.00   59
 38  ω     37.00  90.00   1.00    4.00    --  112.00-111.00-120.00   53
 39  ω     36.00 107.00   1.00    4.00    --  112.00-111.00 150.00   71
 40  ω     84.00 175.00   1.00    4.00    --  112.00  61.00  30.00   91
 41  ω     40.00  88.00   1.00    4.00    --  112.00 -61.00-150.00   48
 42  ω     56.00 109.00   1.00    4.00    --  112.00-111.00 -90.00   53
 43  ω     83.00 111.00   1.00    4.00    --  112.00  61.00 150.00   28
 44  ω     86.00 118.00   1.00    4.00    --  112.00  45.00   0.00   32
 45  ω    120.00 176.00   1.00    4.00    --  112.00  61.00 120.00   56
 46  ω    131.00 169.00   1.00    4.00    --  112.00  61.00-150.00   38
 47  ω     83.00 112.00   1.00    4.00    --  112.00  61.00 120.00   29
 48  ω     83.00 109.00   1.00    4.00    --  112.00  61.00-150.00   26
 49  ω     85.00 161.00   1.00    4.00    --  112.00  61.00 -90.00   76
 50  ω    128.00 160.00   1.00    4.00    --  112.00  61.00-120.00   32
 51  ω     84.00 122.00   1.00    4.00    --  112.00  61.00-120.00   38
 52  ω    124.00 176.00   1.00    4.00    --  112.00  61.00 -30.00   52
 53  ω     82.00 176.00   1.00    4.00    --  112.00  67.00 -64.08   94
 54  ω     95.00 134.00   1.00    4.00    --  112.00 -45.00 -30.00   39
 55  ω     83.00 175.00   1.00    4.00    --  112.00  61.00-180.00   92
 56  ω     88.00 118.00   1.00    4.00    --  112.00  45.00-120.00   30
 57  ω     83.00 112.00   1.00    4.00    --  112.00  61.00 -30.00   29
 58  ω     53.00 108.00   1.00    4.00    --  112.00-111.00  30.00   55
 59  ω     43.00  69.00   1.00    4.00    --  112.00 -45.00 -30.00   26
 60  ω     36.00  90.00   1.00    4.00    --  112.00-111.00-180.00   54
 61  ω    111.00 141.00   1.00    4.00    --  112.00 -61.00-150.00   30
 62  ω     84.00 167.00   1.00    4.00    --  112.00  61.00   0.00   83
 63  ω     83.00 177.00   1.00    4.00    --  112.00  61.00  90.00   94
 64  ω     36.00 106.00   1.00    4.00    --  112.00 -94.00  60.00   70
 65  ω     83.00 178.00   1.00    4.00    --  112.00  61.00  60.00   95
 66  ω    116.00 170.00   1.00    4.00    --  112.00  61.00 150.00   54
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, AtlasS2'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0337195000
_diffrn_orient_matrix_UB_12      -0.0297972000
_diffrn_orient_matrix_UB_13      -0.1389071000
_diffrn_orient_matrix_UB_21      0.0457322000
_diffrn_orient_matrix_UB_22      -0.1142208000
_diffrn_orient_matrix_UB_23      0.0334227000
_diffrn_orient_matrix_UB_31      -0.1812093000
_diffrn_orient_matrix_UB_32      -0.0233073000
_diffrn_orient_matrix_UB_33      0.0137202000
_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  0.0319
_diffrn_reflns_av_unetI/netI     0.0219
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            20912
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.987
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         76.038
_diffrn_reflns_theta_min         4.119
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.620
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.761
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.41.105a (Rigaku Oxford Diffraction, 2021)
Numerical absorption correction based on Gaussian integration over
a multifaceted crystal model.
Empirical absorption correction using spherical harmonics
as implemented in SCALE3 ABSPACK scaling algorithm
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.247
_exptl_crystal_description       plate
_exptl_crystal_F_000             448
_exptl_crystal_size_max          0.36
_exptl_crystal_size_mid          0.17
_exptl_crystal_size_min          0.04
_refine_diff_density_max         0.203
_refine_diff_density_min         -0.157
_refine_diff_density_rms         0.030
_refine_ls_abs_structure_details
;
 Flack x determined using 2130 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.02(7)
_refine_ls_extinction_coef       0.0012(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.057
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     295
_refine_ls_number_reflns         4633
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.057
_refine_ls_R_factor_all          0.0273
_refine_ls_R_factor_gt           0.0268
_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)+(0.0343P)²+0.1923P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0682
_refine_ls_wR_factor_ref         0.0687
_reflns_Friedel_coverage         0.898
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.979
_reflns_number_gt                4564
_reflns_number_total             4633
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            cs1c03153_si_002.cif
_cod_data_source_block           agh-r416
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_exptl_absorpt_correction_type' value 'Gaussian' was
changed to 'gaussian' in accordance with the
/home/data/users/saulius/crontab/automatic-downloads/current/ACS/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 last updated on
2011-04-26.

Automatic conversion script
Id: cif_fix_values 7556 2019-12-06 15:28:31Z antanas 
;
_cod_original_cell_volume        1125.392(17)
_cod_database_code               4519063
_shelx_shelxl_version_number     2018/3
_audit_contact_author            'Farzaneh Fadaei Tirani'
_chemical_oxdiff_formula         'C28 H26 N2 O2'
_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   0.976
_shelx_estimated_absorpt_t_min   0.808
_reflns_odcompleteness_completeness 100.00
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     74.33
_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 Ternary CH refined with riding coordinates:
 C1(H1A), C2(H2)
2.b Secondary CH2 refined with riding coordinates:
 C6(H6A,H6B)
2.c Aromatic/amide H refined with riding coordinates:
 C3(H3), C4(H4), C8(H8), C9(H9), C10(H10), C11(H11), C13(H13), C14(H14),
 C15(H15), C18(H18), C19(H19), C21(H21), C22(H22), C24(H24), C25(H25), C26(H26),
  C27(H27), C28(H28)
2.d Idealised Me refined as rotating group:
 C5(H5A,H5B,H5C)
;
_olex2_date_sample_data_collection 2021-04-14
_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
- B-factor correction
;
_oxdiff_exptl_absorpt_empirical_full_max 2.133
_oxdiff_exptl_absorpt_empirical_full_min 0.544
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 0.57467(16) 0.20117(10) 0.33273(13) 0.0267(3) Uani 1 1 d . . . . .
H1 H 0.519(3) 0.145(2) 0.325(2) 0.037(7) Uiso 1 1 d . . . . .
O2 O 0.75533(15) 0.42141(11) 0.24960(11) 0.0267(3) Uani 1 1 d . . . . .
N1 N 0.69986(17) 0.44256(11) 0.71436(12) 0.0167(3) Uani 1 1 d . . . . .
N2 N 0.55101(18) 0.49077(11) 0.69672(14) 0.0211(3) Uani 1 1 d . . . . .
C1 C 0.60939(19) 0.37247(12) 0.41861(14) 0.0154(3) Uani 1 1 d . . . . .
H1A H 0.558793 0.423813 0.471686 0.018 Uiso 1 1 calc R U . . .
C2 C 0.4903(2) 0.27842(13) 0.39453(15) 0.0178(3) Uani 1 1 d . . . . .
H2 H 0.391329 0.301539 0.336491 0.021 Uiso 1 1 calc R U . . .
C3 C 0.4334(2) 0.23973(14) 0.51219(16) 0.0213(3) Uani 1 1 d . . . . .
H3 H 0.513928 0.215589 0.577462 0.026 Uiso 1 1 calc R U . . .
C4 C 0.2774(2) 0.23758(14) 0.52941(17) 0.0235(4) Uani 1 1 d . . . . .
H4 H 0.198171 0.259040 0.461807 0.028 Uiso 1 1 calc R U . . .
C5 C 0.2143(3) 0.20419(18) 0.64655(19) 0.0334(4) Uani 1 1 d . . . . .
H5A H 0.138523 0.145185 0.628482 0.050 Uiso 1 1 calc R U . . .
H5B H 0.155888 0.262526 0.679482 0.050 Uiso 1 1 calc R U . . .
H5C H 0.307048 0.182993 0.708384 0.050 Uiso 1 1 calc R U . . .
C6 C 0.7781(2) 0.34016(13) 0.48885(15) 0.0175(3) Uani 1 1 d . . . . .
H6A H 0.760742 0.288620 0.553908 0.021 Uiso 1 1 calc R U . . .
H6B H 0.842879 0.305611 0.429754 0.021 Uiso 1 1 calc R U . . .
C7 C 0.87634(19) 0.43124(12) 0.54939(14) 0.0153(3) Uani 1 1 d . . . . .
C8 C 1.0148(2) 0.46901(13) 0.50086(15) 0.0186(3) Uani 1 1 d . . . . .
H8 H 1.045410 0.438191 0.427660 0.022 Uiso 1 1 calc R U . . .
C9 C 1.1084(2) 0.55092(14) 0.55785(16) 0.0202(3) Uani 1 1 d . . . . .
H9 H 1.202102 0.575147 0.523448 0.024 Uiso 1 1 calc R U . . .
C10 C 1.0657(2) 0.59723(14) 0.66435(16) 0.0207(3) Uani 1 1 d . . . . .
H10 H 1.129847 0.653050 0.703078 0.025 Uiso 1 1 calc R U . . .
C11 C 0.9286(2) 0.56167(14) 0.71422(15) 0.0193(3) Uani 1 1 d . . . . .
H11 H 0.898167 0.593075 0.787159 0.023 Uiso 1 1 calc R U . . .
C12 C 0.83632(19) 0.47982(13) 0.65670(14) 0.0151(3) Uani 1 1 d . . . . .
C13 C 0.4590(2) 0.43595(15) 0.76619(16) 0.0238(4) Uani 1 1 d . . . . .
H13 H 0.346678 0.450800 0.772146 0.029 Uiso 1 1 calc R U . . .
C14 C 0.5470(2) 0.35465(16) 0.82871(17) 0.0281(4) Uani 1 1 d . . . . .
H14 H 0.509028 0.305497 0.883981 0.034 Uiso 1 1 calc R U . . .
C15 C 0.7009(2) 0.36110(15) 0.79291(18) 0.0279(4) Uani 1 1 d . . . . .
H15 H 0.791570 0.316292 0.818816 0.033 Uiso 1 1 calc R U . . .
C16 C 0.6280(2) 0.42599(13) 0.29535(14) 0.0172(3) Uani 1 1 d . . . . .
C17 C 0.4823(2) 0.48438(13) 0.22961(15) 0.0161(3) Uani 1 1 d . . . . .
C18 C 0.3458(2) 0.51128(13) 0.28767(15) 0.0184(3) Uani 1 1 d . . . . .
H18 H 0.342917 0.492042 0.372021 0.022 Uiso 1 1 calc R U . . .
C19 C 0.2149(2) 0.56568(14) 0.22327(15) 0.0196(3) Uani 1 1 d . . . . .
H19 H 0.123226 0.583284 0.264194 0.023 Uiso 1 1 calc R U . . .
C20 C 0.2153(2) 0.59521(13) 0.09898(15) 0.0170(3) Uani 1 1 d . . . . .
C21 C 0.3522(2) 0.56828(13) 0.04143(14) 0.0189(3) Uani 1 1 d . . . . .
H21 H 0.355373 0.587776 -0.042798 0.023 Uiso 1 1 calc R U . . .
C22 C 0.4830(2) 0.51363(14) 0.10544(15) 0.0187(3) Uani 1 1 d . . . . .
H22 H 0.574553 0.495771 0.064433 0.022 Uiso 1 1 calc R U . . .
C23 C 0.0750(2) 0.65627(12) 0.03314(14) 0.0172(3) Uani 1 1 d . . . . .
C24 C -0.0858(2) 0.63647(14) 0.05544(16) 0.0213(4) Uani 1 1 d . . . . .
H24 H -0.106883 0.580985 0.109307 0.026 Uiso 1 1 calc R U . . .
C25 C -0.2155(2) 0.69750(16) -0.00075(16) 0.0253(4) Uani 1 1 d . . . . .
H25 H -0.324868 0.683143 0.014380 0.030 Uiso 1 1 calc R U . . .
C26 C -0.1862(2) 0.77924(15) -0.07880(17) 0.0262(4) Uani 1 1 d . . . . .
H26 H -0.274801 0.821906 -0.115311 0.031 Uiso 1 1 calc R U . . .
C27 C -0.0271(2) 0.79852(14) -0.10339(16) 0.0237(4) Uani 1 1 d . . . . .
H27 H -0.006834 0.853832 -0.157735 0.028 Uiso 1 1 calc R U . . .
C28 C 0.1027(2) 0.73699(13) -0.04859(15) 0.0200(3) Uani 1 1 d . . . . .
H28 H 0.211152 0.749815 -0.066748 0.024 Uiso 1 1 calc R U . . .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
0 1 0 0.1886
0 -1 0 0.1713
0 0 1 0.0172
0 0 -1 0.0229
-1 0 0 0.0733
1 0 0 0.0872
1 -1 0 0.0887
2 2 -1 0.0946
-2 1 0 0.0971
-2 -1 1 0.1003
1 -2 1 0.0956
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
C2 O1 H1 110.2(18) . . ?
N2 N1 C12 121.73(13) . . ?
C15 N1 N2 111.68(14) . . ?
C15 N1 C12 126.56(15) . . ?
C13 N2 N1 104.30(14) . . ?
C2 C1 H1A 107.9 . . ?
C6 C1 H1A 107.9 . . ?
C6 C1 C2 112.09(13) . . ?
C16 C1 H1A 107.9 . . ?
C16 C1 C2 109.71(12) . . ?
C16 C1 C6 111.27(13) . . ?
O1 C2 C1 106.49(13) . . ?
O1 C2 H2 108.3 . . ?
O1 C2 C3 113.40(14) . . ?
C1 C2 H2 108.3 . . ?
C3 C2 C1 112.04(13) . . ?
C3 C2 H2 108.3 . . ?
C2 C3 H3 118.4 . . ?
C4 C3 C2 123.20(16) . . ?
C4 C3 H3 118.4 . . ?
C3 C4 H4 117.3 . . ?
C3 C4 C5 125.49(18) . . ?
C5 C4 H4 117.3 . . ?
C4 C5 H5A 109.5 . . ?
C4 C5 H5B 109.5 . . ?
C4 C5 H5C 109.5 . . ?
H5A C5 H5B 109.5 . . ?
H5A C5 H5C 109.5 . . ?
H5B C5 H5C 109.5 . . ?
C1 C6 H6A 108.9 . . ?
C1 C6 H6B 108.9 . . ?
H6A C6 H6B 107.7 . . ?
C7 C6 C1 113.25(13) . . ?
C7 C6 H6A 108.9 . . ?
C7 C6 H6B 108.9 . . ?
C8 C7 C6 120.86(14) . . ?
C12 C7 C6 122.16(14) . . ?
C12 C7 C8 116.97(14) . . ?
C7 C8 H8 119.4 . . ?
C9 C8 C7 121.25(15) . . ?
C9 C8 H8 119.4 . . ?
C8 C9 H9 119.8 . . ?
C10 C9 C8 120.36(15) . . ?
C10 C9 H9 119.8 . . ?
C9 C10 H10 120.2 . . ?
C9 C10 C11 119.63(16) . . ?
C11 C10 H10 120.2 . . ?
C10 C11 H11 120.3 . . ?
C10 C11 C12 119.50(15) . . ?
C12 C11 H11 120.3 . . ?
C7 C12 N1 120.00(14) . . ?
C11 C12 N1 117.65(14) . . ?
C11 C12 C7 122.29(15) . . ?
N2 C13 H13 124.0 . . ?
N2 C13 C14 111.95(16) . . ?
C14 C13 H13 124.0 . . ?
C13 C14 H14 127.7 . . ?
C15 C14 C13 104.63(16) . . ?
C15 C14 H14 127.7 . . ?
N1 C15 C14 107.43(16) . . ?
N1 C15 H15 126.3 . . ?
C14 C15 H15 126.3 . . ?
O2 C16 C1 121.91(14) . . ?
O2 C16 C17 120.02(14) . . ?
C17 C16 C1 118.06(13) . . ?
C18 C17 C16 122.74(14) . . ?
C22 C17 C16 118.83(14) . . ?
C22 C17 C18 118.43(15) . . ?
C17 C18 H18 119.7 . . ?
C19 C18 C17 120.57(15) . . ?
C19 C18 H18 119.7 . . ?
C18 C19 H19 119.4 . . ?
C18 C19 C20 121.17(15) . . ?
C20 C19 H19 119.4 . . ?
C19 C20 C23 120.02(15) . . ?
C21 C20 C19 118.03(15) . . ?
C21 C20 C23 121.93(15) . . ?
C20 C21 H21 119.5 . . ?
C22 C21 C20 120.94(15) . . ?
C22 C21 H21 119.5 . . ?
C17 C22 H22 119.6 . . ?
C21 C22 C17 120.85(15) . . ?
C21 C22 H22 119.6 . . ?
C24 C23 C20 120.44(15) . . ?
C24 C23 C28 118.85(15) . . ?
C28 C23 C20 120.67(16) . . ?
C23 C24 H24 119.8 . . ?
C25 C24 C23 120.33(16) . . ?
C25 C24 H24 119.8 . . ?
C24 C25 H25 119.8 . . ?
C26 C25 C24 120.36(17) . . ?
C26 C25 H25 119.8 . . ?
C25 C26 H26 120.1 . . ?
C25 C26 C27 119.79(17) . . ?
C27 C26 H26 120.1 . . ?
C26 C27 H27 120.0 . . ?
C26 C27 C28 120.05(16) . . ?
C28 C27 H27 120.0 . . ?
C23 C28 H28 119.7 . . ?
C27 C28 C23 120.57(16) . . ?
C27 C28 H28 119.7 . . ?
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 0.85(3) . ?
O1 C2 1.425(2) . ?
O2 C16 1.216(2) . ?
N1 N2 1.356(2) . ?
N1 C12 1.435(2) . ?
N1 C15 1.345(2) . ?
N2 C13 1.335(2) . ?
C1 H1A 1.0000 . ?
C1 C2 1.549(2) . ?
C1 C6 1.540(2) . ?
C1 C16 1.527(2) . ?
C2 H2 1.0000 . ?
C2 C3 1.500(2) . ?
C3 H3 0.9500 . ?
C3 C4 1.317(2) . ?
C4 H4 0.9500 . ?
C4 C5 1.497(3) . ?
C5 H5A 0.9800 . ?
C5 H5B 0.9800 . ?
C5 H5C 0.9800 . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C6 C7 1.514(2) . ?
C7 C8 1.400(2) . ?
C7 C12 1.397(2) . ?
C8 H8 0.9500 . ?
C8 C9 1.393(2) . ?
C9 H9 0.9500 . ?
C9 C10 1.384(2) . ?
C10 H10 0.9500 . ?
C10 C11 1.387(2) . ?
C11 H11 0.9500 . ?
C11 C12 1.389(2) . ?
C13 H13 0.9500 . ?
C13 C14 1.388(3) . ?
C14 H14 0.9500 . ?
C14 C15 1.371(3) . ?
C15 H15 0.9500 . ?
C16 C17 1.502(2) . ?
C17 C18 1.399(2) . ?
C17 C22 1.397(2) . ?
C18 H18 0.9500 . ?
C18 C19 1.384(2) . ?
C19 H19 0.9500 . ?
C19 C20 1.399(2) . ?
C20 C21 1.399(2) . ?
C20 C23 1.488(2) . ?
C21 H21 0.9500 . ?
C21 C22 1.384(3) . ?
C22 H22 0.9500 . ?
C23 C24 1.395(2) . ?
C23 C28 1.400(2) . ?
C24 H24 0.9500 . ?
C24 C25 1.390(2) . ?
C25 H25 0.9500 . ?
C25 C26 1.387(3) . ?
C26 H26 0.9500 . ?
C26 C27 1.388(3) . ?
C27 H27 0.9500 . ?
C27 C28 1.389(3) . ?
C28 H28 0.9500 . ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
C1 H1A N2 1.00 2.59 3.464(2) 145.4 . yes
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 C2 C3 C4 -119.42(18) . . . . ?
O2 C16 C17 C18 -166.29(16) . . . . ?
O2 C16 C17 C22 13.4(2) . . . . ?
N1 N2 C13 C14 0.70(19) . . . . ?
N2 N1 C12 C7 -100.26(18) . . . . ?
N2 N1 C12 C11 82.31(19) . . . . ?
N2 N1 C15 C14 0.1(2) . . . . ?
N2 C13 C14 C15 -0.6(2) . . . . ?
C1 C2 C3 C4 120.00(18) . . . . ?
C1 C6 C7 C8 -107.49(17) . . . . ?
C1 C6 C7 C12 73.93(19) . . . . ?
C1 C16 C17 C18 14.5(2) . . . . ?
C1 C16 C17 C22 -165.83(15) . . . . ?
C2 C1 C6 C7 -161.64(13) . . . . ?
C2 C1 C16 O2 -109.83(18) . . . . ?
C2 C1 C16 C17 69.39(17) . . . . ?
C2 C3 C4 C5 -177.23(17) . . . . ?
C6 C1 C2 O1 -54.10(17) . . . . ?
C6 C1 C2 C3 70.41(17) . . . . ?
C6 C1 C16 O2 14.8(2) . . . . ?
C6 C1 C16 C17 -165.99(13) . . . . ?
C6 C7 C8 C9 -178.27(15) . . . . ?
C6 C7 C12 N1 1.0(2) . . . . ?
C6 C7 C12 C11 178.35(15) . . . . ?
C7 C8 C9 C10 -0.2(3) . . . . ?
C8 C7 C12 N1 -177.58(14) . . . . ?
C8 C7 C12 C11 -0.3(2) . . . . ?
C8 C9 C10 C11 -0.1(3) . . . . ?
C9 C10 C11 C12 0.2(3) . . . . ?
C10 C11 C12 N1 177.38(15) . . . . ?
C10 C11 C12 C7 0.0(2) . . . . ?
C12 N1 N2 C13 -178.65(14) . . . . ?
C12 N1 C15 C14 178.17(16) . . . . ?
C12 C7 C8 C9 0.4(2) . . . . ?
C13 C14 C15 N1 0.3(2) . . . . ?
C15 N1 N2 C13 -0.51(19) . . . . ?
C15 N1 C12 C7 81.9(2) . . . . ?
C15 N1 C12 C11 -95.5(2) . . . . ?
C16 C1 C2 O1 70.04(16) . . . . ?
C16 C1 C2 C3 -165.45(13) . . . . ?
C16 C1 C6 C7 75.08(17) . . . . ?
C16 C17 C18 C19 179.63(16) . . . . ?
C16 C17 C22 C21 -179.46(15) . . . . ?
C17 C18 C19 C20 0.0(3) . . . . ?
C18 C17 C22 C21 0.2(2) . . . . ?
C18 C19 C20 C21 -0.1(3) . . . . ?
C18 C19 C20 C23 -178.27(16) . . . . ?
C19 C20 C21 C22 0.3(3) . . . . ?
C19 C20 C23 C24 -37.1(2) . . . . ?
C19 C20 C23 C28 140.57(17) . . . . ?
C20 C21 C22 C17 -0.4(3) . . . . ?
C20 C23 C24 C25 176.34(16) . . . . ?
C20 C23 C28 C27 -175.59(15) . . . . ?
C21 C20 C23 C24 144.85(17) . . . . ?
C21 C20 C23 C28 -37.5(2) . . . . ?
C22 C17 C18 C19 -0.1(2) . . . . ?
C23 C20 C21 C22 178.41(16) . . . . ?
C23 C24 C25 C26 -0.5(3) . . . . ?
C24 C23 C28 C27 2.1(2) . . . . ?
C24 C25 C26 C27 1.6(3) . . . . ?
C25 C26 C27 C28 -0.9(3) . . . . ?
C26 C27 C28 C23 -1.0(3) . . . . ?
C28 C23 C24 C25 -1.3(3) . . . . ?
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
0.0000 1.0000 -0.0000 -0.0298 -0.1142 -0.0233
-0.0000 -1.0000 0.0000 0.0298 0.1142 0.0233
-0.0000 -0.0000 1.0000 -0.1389 0.0334 0.0137
0.0000 0.0000 -1.0000 0.1389 -0.0334 -0.0137
-1.0000 0.0000 0.0000 0.0337 -0.0457 0.1812
1.0000 -0.0000 -0.0000 -0.0337 0.0457 -0.1812
1.0000 -1.0000 0.0000 -0.0039 0.1600 -0.1579
2.0000 2.0000 -1.0000 0.0119 -0.1704 -0.4228
-2.0000 1.0000 0.0000 0.0376 -0.2057 0.3391
-2.0000 -1.0000 1.0000 -0.0417 0.0562 0.3994
1.0000 -2.0000 1.0000 -0.1130 0.3076 -0.1209
