#------------------------------------------------------------------------------
#$Date: 2021-05-05 11:59:25 +0300 (Wed, 05 May 2021) $
#$Revision: 264937 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/06/04/7060470.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_7060470
loop_
_publ_author_name
'Kukkonen, Esa'
'Lahtinen, Elmeri'
'Myllyperkiö, Pasi'
'Haukka, Matti'
'Konu, Jari'
_publ_section_title
;
 Nonlinear optical properties of diaromatic stilbene, butadiene and
 thiophene derivatives
;
_journal_issue                   15
_journal_name_full               'New Journal of Chemistry'
_journal_page_first              6640
_journal_page_last               6650
_journal_paper_doi               10.1039/D1NJ00456E
_journal_volume                  45
_journal_year                    2021
_chemical_formula_moiety         'C16 H16 N2 O2'
_chemical_formula_sum            'C16 H16 N2 O2'
_chemical_formula_weight         268.31
_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     dual
_audit_creation_date             2021-03-04
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2021-03-12 deposited with the CCDC.	2021-03-19 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 96.417(7)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   5.9378(4)
_cell_length_b                   7.3721(7)
_cell_length_c                   15.3569(12)
_cell_measurement_reflns_used    1219
_cell_measurement_temperature    120.01(10)
_cell_measurement_theta_max      74.6780
_cell_measurement_theta_min      2.8290
_cell_volume                     668.02(9)
_computing_cell_refinement       'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43 (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    'ShelXD (Sheldrick, 2008)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      120.01(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.1977
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.973
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -95.00 -51.00   1.00   10.00    --  -41.65 125.00-180.00   44
  2  ω    -67.00  24.00   1.00   10.00    --  -41.65  57.00 120.00   91
  3  ω    -66.00  33.00   1.00   10.00    --  -41.65  37.00 -90.00   99
  4  ω   -113.00 -20.00   1.00   10.00    --  -41.65 -57.00 -30.00   93
  5  ω    106.00 163.00   1.00   80.00    --  112.00 111.00 -30.00   57
  6  ω     45.00 116.00   1.00   80.00    --  112.00-111.00  60.00   71
  7  ω     39.00 129.00   1.00   80.00    --  112.00 -77.00-120.00   90
  8  ω     45.00 109.00   1.00   80.00    --  112.00 -94.00-180.00   64
  9  ω    101.00 168.00   1.00   80.00    --  112.00  77.00  60.00   67
 10  ω     49.00 125.00   1.00   80.00    --  112.00 -45.00   0.00   76
 11  ω     82.00 108.00   1.00   80.00    --  112.00  77.00 120.00   26
 12  ω    132.00 176.00   1.00   80.00    --  112.00  77.00 120.00   44
 13  ω     86.00 173.00   1.00   80.00    --  112.00  45.00  30.00   87
 14  ω    102.00 172.00   1.00   80.00    --  112.00  61.00 -60.00   70
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.1336932000
_diffrn_orient_matrix_UB_12      -0.1766289000
_diffrn_orient_matrix_UB_13      0.0100555000
_diffrn_orient_matrix_UB_21      0.2205563000
_diffrn_orient_matrix_UB_22      -0.0961701000
_diffrn_orient_matrix_UB_23      0.0367385000
_diffrn_orient_matrix_UB_31      -0.0409957000
_diffrn_orient_matrix_UB_32      0.0566809000
_diffrn_orient_matrix_UB_33      0.0934656000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0322
_diffrn_reflns_av_unetI/netI     0.0437
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.973
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            3947
_diffrn_reflns_point_group_measured_fraction_full 0.813
_diffrn_reflns_point_group_measured_fraction_max 0.780
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         76.761
_diffrn_reflns_theta_min         2.896
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.719
_exptl_absorpt_correction_T_max  0.971
_exptl_absorpt_correction_T_min  0.922
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.43 (Rigaku Oxford Diffraction, 2015)
Analytical numeric absorption correction using a multifaceted crystal
			model based on expressions derived by R.C. Clark & J.S. Reid.
(Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            red
_exptl_crystal_colour_primary    red
_exptl_crystal_density_diffrn    1.334
_exptl_crystal_description       block
_exptl_crystal_F_000             284
_exptl_crystal_size_max          0.126
_exptl_crystal_size_mid          0.054
_exptl_crystal_size_min          0.034
_refine_diff_density_max         0.356
_refine_diff_density_min         -0.293
_refine_diff_density_rms         0.058
_refine_ls_abs_structure_details
;
 Flack x determined using 410 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.2(10)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.101
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     217
_refine_ls_number_reflns         2194
_refine_ls_number_restraints     4
_refine_ls_restrained_S_all      1.109
_refine_ls_R_factor_all          0.1051
_refine_ls_R_factor_gt           0.0855
_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)+(0.1281P)²+0.3516P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2365
_refine_ls_wR_factor_ref         0.2602
_reflns_Friedel_coverage         0.483
_reflns_Friedel_fraction_full    0.595
_reflns_Friedel_fraction_max     0.553
_reflns_number_gt                1671
_reflns_number_total             2194
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d1nj00456e2.cif
_cod_data_source_block           compound_1e
_cod_depositor_comments
'Adding full bibliography for 7060468--7060480.cif.'
_cod_database_code               7060470
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C11 H10 N O'
_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 99.57
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     69.95
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 C8B-C7B
 1.3 with sigma of 0.02
 C9-C8B
 1.4 with sigma of 0.02
 C7B-C4
 1.4 with sigma of 0.02
3. Uiso/Uaniso restraints and constraints
Uanis(C8B) = Uanis(C7B)
Uanis(C13B) = Uanis(C14B) = Uanis(C10B) = Uanis(C11B)
Uanis(C13A) = Uanis(C14A) = Uanis(C10A) = Uanis(C11A)
Uanis(O2B) = Uanis(O1B)
Uanis(C3B) = Uanis(C2B) = Uanis(C6B) = Uanis(C5B)
Uanis(C16B) = Uanis(C15B)
Uanis(C5A) = Uanis(C6A) = Uanis(C2A) = Uanis(C3A)
4. Others
 Fixed Sof: O1A(0.6) O2A(0.6) C2A(0.6) H2A(0.6) C3A(0.6) H3A(0.6) C5A(0.6)
 H5A(0.6) C6A(0.6) H6A(0.6) C7A(0.75) H7A(0.75) C8A(0.75) H8A(0.75) C10A(0.6)
 H10A(0.6) C11A(0.6) H11A(0.6) C13A(0.6) H13A(0.6) C14A(0.6) H14A(0.6)
 C15A(0.6) H15A(0.6) H15B(0.6) H15C(0.6) C16A(0.6) H16A(0.6) H16B(0.6)
 H16C(0.6) O1B(0.4) O2B(0.4) C3B(0.4) H3B(0.4) C2B(0.4) H2B(0.4) C6B(0.4)
 H6B(0.4) C5B(0.4) H5B(0.4) C7B(0.25) H7B(0.25) C8B(0.25) H8B(0.25) C11B(0.4)
 H11B(0.4) C10B(0.4) H10B(0.4) C14B(0.4) H14B(0.4) C13B(0.4) H13B(0.4)
 C15B(0.4) H15D(0.4) H15E(0.4) H15F(0.4) C16B(0.4) H16D(0.4) H16E(0.4) H16F(0.4)
5.a Me refined with riding coordinates:
 C15A(H15A,H15B,H15C), C16A(H16A,H16B,H16C), C15B(H15D,H15E,H15F), C16B(H16D,
 H16E,H16F)
5.b Aromatic/amide H refined with riding coordinates:
 C2A(H2A), C3A(H3A), C5A(H5A), C6A(H6A), C7A(H7A), C8A(H8A), C10A(H10A),
 C11A(H11A), C13A(H13A), C14A(H14A), C3B(H3B), C2B(H2B), C6B(H6B), C5B(H5B),
 C7B(H7B), C8B(H8B), C11B(H11B), C10B(H10B), C14B(H14B), C13B(H13B)
;
_ins_header
;
TITL ek1918_a_P21 in P2(1) 
REM P2(1) (#4 in standard setting)
CELL 1.54184   5.937789   7.372117  15.356879  90.0000  96.4174  90.0000
ZERR    3.00   0.000429   0.000681   0.001194   0.0000   0.0066   0.0000
LATT -1
SYMM -x, y+1/2,-z 
SFAC C H N O
UNIT 33.00 30.00 3.00 3.00
TREF
HKLF 4
END
;
_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 1.308
_oxdiff_exptl_absorpt_empirical_full_min 0.758
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
N1 N 1.1144(6) 1.6311(9) 1.1436(2) 0.0401(9) Uani 1 1 d . . . . .
N2 N 0.4092(5) 1.6271(8) 1.86395(19) 0.0360(8) Uani 1 1 d . . . . .
O1A O 0.9980(15) 1.7130(15) 1.0847(5) 0.066(2) Uani 0.6 1 d . . P A 1
O2A O 1.2888(15) 1.5550(16) 1.1317(7) 0.075(3) Uani 0.6 1 d . . P A 1
C2A C 1.1709(13) 1.5470(11) 1.2969(7) 0.0365(11) Uani 0.6 1 d . . P B 1
H2A H 1.307268 1.494259 1.285979 0.044 Uiso 0.6 1 calc R . P B 1
C3A C 1.1074(14) 1.5425(11) 1.3780(7) 0.0365(11) Uani 0.6 1 d . . P B 1
H3A H 1.199513 1.484518 1.422480 0.044 Uiso 0.6 1 calc R . P B 1
C5A C 0.7612(13) 1.7104(10) 1.3264(7) 0.0365(11) Uani 0.6 1 d . . P B 1
H5A H 0.623012 1.762189 1.335613 0.044 Uiso 0.6 1 calc R . P B 1
C6A C 0.8342(14) 1.7147(10) 1.2436(7) 0.0365(11) Uani 0.6 1 d . . P B 1
H6A H 0.749402 1.774125 1.197601 0.044 Uiso 0.6 1 calc R . P B 1
C7A C 0.8455(8) 1.6140(14) 1.4883(3) 0.0347(14) Uani 0.75 1 d . . P B 1
H7A H 0.965914 1.587822 1.530506 0.042 Uiso 0.75 1 calc R . P B 1
C8A C 0.6484(9) 1.6360(14) 1.5168(3) 0.0331(13) Uani 0.75 1 d . . P B 1
H8A H 0.526467 1.657312 1.474573 0.040 Uiso 0.75 1 calc R . P B 1
C10A C 0.7301(13) 1.5535(11) 1.6729(6) 0.0328(10) Uani 0.6 1 d . . P B 1
H10A H 0.864598 1.499270 1.660887 0.039 Uiso 0.6 1 calc R . P B 1
C11A C 0.6758(14) 1.5495(11) 1.7607(6) 0.0328(10) Uani 0.6 1 d . . P B 1
H11A H 0.773930 1.495199 1.804486 0.039 Uiso 0.6 1 calc R . P B 1
C13A C 0.3360(14) 1.7095(11) 1.7093(6) 0.0328(10) Uani 0.6 1 d . . P B 1
H13A H 0.201271 1.766019 1.719229 0.039 Uiso 0.6 1 calc R . P B 1
C14A C 0.4013(13) 1.7057(11) 1.6239(6) 0.0328(10) Uani 0.6 1 d . . P B 1
H14A H 0.305435 1.756202 1.578276 0.039 Uiso 0.6 1 calc R . P B 1
C15A C 0.2261(17) 1.7418(17) 1.8843(8) 0.049(2) Uani 0.6 1 d . . P C 1
H15A H 0.202295 1.725683 1.944659 0.073 Uiso 0.6 1 calc R . P C 1
H15B H 0.263500 1.866251 1.874405 0.073 Uiso 0.6 1 calc R . P C 1
H15C H 0.090392 1.710073 1.847541 0.073 Uiso 0.6 1 calc R . P C 1
C16A C 0.566(3) 1.564(3) 1.9368(9) 0.076(5) Uani 0.6 1 d . . P C 1
H16A H 0.496194 1.571934 1.990006 0.115 Uiso 0.6 1 calc R . P C 1
H16B H 0.606713 1.440102 1.926867 0.115 Uiso 0.6 1 calc R . P C 1
H16C H 0.700257 1.637877 1.941632 0.115 Uiso 0.6 1 calc R . P C 1
O1B O 0.997(2) 1.5314(18) 1.0857(6) 0.0522(19) Uani 0.4 1 d . . P A 2
O2B O 1.288(2) 1.6973(19) 1.1329(6) 0.0522(19) Uani 0.4 1 d . . P A 2
C3B C 1.091(2) 1.712(2) 1.3807(7) 0.0382(16) Uani 0.4 1 d . . P B 2
H3B H 1.173554 1.774455 1.426332 0.046 Uiso 0.4 1 calc R . P B 2
C2B C 1.172(2) 1.713(2) 1.2972(7) 0.0382(16) Uani 0.4 1 d . . P B 2
H2B H 1.308254 1.768448 1.288023 0.046 Uiso 0.4 1 calc R . P B 2
C1 C 1.0374(6) 1.6281(8) 1.2306(2) 0.0291(8) Uani 1 1 d . . . . .
C6B C 0.837(3) 1.5409(19) 1.2426(7) 0.0382(16) Uani 0.4 1 d . . P B 2
H6B H 0.748567 1.481635 1.197409 0.046 Uiso 0.4 1 calc R . P B 2
C5B C 0.774(2) 1.5493(19) 1.3306(7) 0.0382(16) Uani 0.4 1 d . . P B 2
H5B H 0.637166 1.497440 1.341109 0.046 Uiso 0.4 1 calc R . P B 2
C4 C 0.8995(7) 1.6258(10) 1.3976(3) 0.0399(10) Uani 1 1 d D . . . .
C7B C 0.724(4) 1.658(7) 1.4563(13) 0.087(8) Uani 0.25 1 d D . P B 2
H7B H 0.586562 1.710244 1.434111 0.105 Uiso 0.25 1 calc R . P B 2
C8B C 0.757(4) 1.615(7) 1.5376(14) 0.087(8) Uani 0.25 1 d D . P B 2
H8B H 0.899263 1.567652 1.556356 0.105 Uiso 0.25 1 calc R . P B 2
C11B C 0.681(2) 1.703(2) 1.7625(7) 0.0375(16) Uani 0.4 1 d . . P B 2
H11B H 0.775823 1.752747 1.808707 0.045 Uiso 0.4 1 calc R . P B 2
C10B C 0.750(2) 1.7081(19) 1.6803(7) 0.0375(16) Uani 0.4 1 d . . P B 2
H10B H 0.889063 1.758716 1.671276 0.045 Uiso 0.4 1 calc R . P B 2
C9 C 0.5990(7) 1.6309(9) 1.6062(2) 0.0374(10) Uani 1 1 d D . . . .
C14B C 0.386(2) 1.547(2) 1.6285(7) 0.0375(16) Uani 0.4 1 d . . P B 2
H14B H 0.287038 1.493431 1.584621 0.045 Uiso 0.4 1 calc R . P B 2
C13B C 0.334(2) 1.548(2) 1.7111(8) 0.0375(16) Uani 0.4 1 d . . P B 2
H13B H 0.199660 1.492504 1.723091 0.045 Uiso 0.4 1 calc R . P B 2
C12 C 0.4735(6) 1.6279(8) 1.7804(2) 0.0289(8) Uani 1 1 d . . . . .
C15B C 0.232(3) 1.507(2) 1.8855(8) 0.046(3) Uani 0.4 1 d . . P C 2
H15D H 0.208318 1.523779 1.945804 0.069 Uiso 0.4 1 calc R . P C 2
H15E H 0.094306 1.534539 1.848816 0.069 Uiso 0.4 1 calc R . P C 2
H15F H 0.274854 1.383936 1.876150 0.069 Uiso 0.4 1 calc R . P C 2
C16B C 0.584(3) 1.665(3) 1.9357(10) 0.046(3) Uani 0.4 1 d . . P C 2
H16D H 0.518954 1.660285 1.990205 0.069 Uiso 0.4 1 calc R . P C 2
H16E H 0.701653 1.575393 1.936196 0.069 Uiso 0.4 1 calc R . P C 2
H16F H 0.646067 1.783001 1.928133 0.069 Uiso 0.4 1 calc R . P C 2
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 -6 0.0165
-3 -1 -2 0.0385
0 1 6 0.0175
3 1 2 0.0565
0 -1 0 0.0235
0 1 0 0.0175
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
O1A N1 C1 118.1(6) . . ?
O2A N1 O1A 122.4(7) . . ?
O2A N1 C1 119.4(6) . . ?
O1B N1 C1 114.9(6) . . ?
O2B N1 O1B 123.7(8) . . ?
O2B N1 C1 120.4(6) . . ?
C15A N2 C16A 117.2(7) . . ?
C12 N2 C15A 119.6(6) . . ?
C12 N2 C16A 119.8(6) . . ?
C12 N2 C15B 120.1(7) . . ?
C12 N2 C16B 117.2(7) . . ?
C15B N2 C16B 114.9(9) . . ?
C3A C2A H2A 119.8 . . ?
C3A C2A C1 120.4(7) . . ?
C1 C2A H2A 119.8 . . ?
C2A C3A H3A 119.4 . . ?
C2A C3A C4 121.3(8) . . ?
C4 C3A H3A 119.4 . . ?
C6A C5A H5A 120.1 . . ?
C6A C5A C4 119.8(6) . . ?
C4 C5A H5A 120.1 . . ?
C5A C6A H6A 120.6 . . ?
C5A C6A C1 118.9(8) . . ?
C1 C6A H6A 120.6 . . ?
C8A C7A H7A 116.2 . . ?
C8A C7A C4 127.7(5) . . ?
C4 C7A H7A 116.2 . . ?
C7A C8A H8A 116.4 . . ?
C7A C8A C9 127.2(5) . . ?
C9 C8A H8A 116.4 . . ?
C11A C10A H10A 118.0 . . ?
C9 C10A H10A 118.0 . . ?
C9 C10A C11A 124.0(7) . . ?
C10A C11A H11A 120.4 . . ?
C12 C11A C10A 119.3(7) . . ?
C12 C11A H11A 120.4 . . ?
C14A C13A H13A 119.6 . . ?
C14A C13A C12 120.8(7) . . ?
C12 C13A H13A 119.6 . . ?
C13A C14A H14A 119.0 . . ?
C9 C14A C13A 122.1(8) . . ?
C9 C14A H14A 119.0 . . ?
N2 C15A H15A 109.5 . . ?
N2 C15A H15B 109.5 . . ?
N2 C15A H15C 109.5 . . ?
H15A C15A H15B 109.5 . . ?
H15A C15A H15C 109.5 . . ?
H15B C15A H15C 109.5 . . ?
N2 C16A H16A 109.5 . . ?
N2 C16A H16B 109.5 . . ?
N2 C16A H16C 109.5 . . ?
H16A C16A H16B 109.5 . . ?
H16A C16A H16C 109.5 . . ?
H16B C16A H16C 109.5 . . ?
C2B C3B H3B 118.2 . . ?
C4 C3B H3B 118.2 . . ?
C4 C3B C2B 123.5(12) . . ?
C3B C2B H2B 121.9 . . ?
C1 C2B C3B 116.2(12) . . ?
C1 C2B H2B 121.9 . . ?
C2A C1 N1 118.5(5) . . ?
C2A C1 C6A 122.3(6) . . ?
C6A C1 N1 119.2(5) . . ?
C2B C1 N1 117.3(6) . . ?
C2B C1 C6B 123.3(7) . . ?
C6B C1 N1 119.4(5) . . ?
C1 C6B H6B 122.6 . . ?
C1 C6B C5B 114.8(10) . . ?
C5B C6B H6B 122.6 . . ?
C6B C5B H5B 117.8 . . ?
C4 C5B C6B 124.4(12) . . ?
C4 C5B H5B 117.8 . . ?
C3A C4 C7A 117.2(6) . . ?
C5A C4 C3A 117.2(6) . . ?
C5A C4 C7A 125.6(6) . . ?
C3B C4 C7B 135.1(19) . . ?
C5B C4 C3B 117.6(8) . . ?
C5B C4 C7B 99.7(13) . . ?
C4 C7B H7B 119.5 . . ?
C8B C7B C4 121(2) . . ?
C8B C7B H7B 119.5 . . ?
C7B C8B H8B 115.5 . . ?
C7B C8B C9 129(2) . . ?
C9 C8B H8B 115.5 . . ?
C10B C11B H11B 118.3 . . ?
C10B C11B C12 123.3(11) . . ?
C12 C11B H11B 118.3 . . ?
C11B C10B H10B 120.7 . . ?
C11B C10B C9 118.6(10) . . ?
C9 C10B H10B 120.7 . . ?
C10A C9 C8A 125.3(6) . . ?
C10A C9 C14A 117.6(6) . . ?
C14A C9 C8A 117.2(6) . . ?
C10B C9 C8B 101.4(13) . . ?
C10B C9 C14B 116.3(7) . . ?
C14B C9 C8B 138.7(18) . . ?
C9 C14B H14B 119.6 . . ?
C13B C14B C9 120.7(11) . . ?
C13B C14B H14B 119.6 . . ?
C14B C13B H13B 118.7 . . ?
C14B C13B C12 122.7(12) . . ?
C12 C13B H13B 118.7 . . ?
N2 C12 C11A 122.3(5) . . ?
N2 C12 C13A 121.4(5) . . ?
N2 C12 C11B 121.6(6) . . ?
N2 C12 C13B 120.1(6) . . ?
C11A C12 C13A 116.3(6) . . ?
C13B C12 C11B 118.3(8) . . ?
N2 C15B H15D 109.5 . . ?
N2 C15B H15E 109.5 . . ?
N2 C15B H15F 109.5 . . ?
H15D C15B H15E 109.5 . . ?
H15D C15B H15F 109.5 . . ?
H15E C15B H15F 109.5 . . ?
N2 C16B H16D 109.5 . . ?
N2 C16B H16E 109.5 . . ?
N2 C16B H16F 109.5 . . ?
H16D C16B H16E 109.5 . . ?
H16D C16B H16F 109.5 . . ?
H16E C16B H16F 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
N1 O1A 1.233(10) . ?
N1 O2A 1.209(10) . ?
N1 O1B 1.294(14) . ?
N1 O2B 1.168(14) . ?
N1 C1 1.460(4) . ?
N2 C15A 1.439(12) . ?
N2 C16A 1.451(14) . ?
N2 C12 1.379(4) . ?
N2 C15B 1.440(15) . ?
N2 C16B 1.453(17) . ?
C2A H2A 0.9300 . ?
C2A C3A 1.342(13) . ?
C2A C1 1.357(10) . ?
C3A H3A 0.9300 . ?
C3A C4 1.440(9) . ?
C5A H5A 0.9300 . ?
C5A C6A 1.388(13) . ?
C5A C4 1.435(11) . ?
C6A H6A 0.9300 . ?
C6A C1 1.399(9) . ?
C7A H7A 0.9300 . ?
C7A C8A 1.304(7) . ?
C7A C4 1.467(6) . ?
C8A H8A 0.9300 . ?
C8A C9 1.436(6) . ?
C10A H10A 0.9300 . ?
C10A C11A 1.421(12) . ?
C10A C9 1.342(10) . ?
C11A H11A 0.9300 . ?
C11A C12 1.397(9) . ?
C13A H13A 0.9300 . ?
C13A C14A 1.408(12) . ?
C13A C12 1.422(10) . ?
C14A H14A 0.9300 . ?
C14A C9 1.351(10) . ?
C15A H15A 0.9600 . ?
C15A H15B 0.9600 . ?
C15A H15C 0.9600 . ?
C16A H16A 0.9600 . ?
C16A H16B 0.9600 . ?
C16A H16C 0.9600 . ?
C3B H3B 0.9300 . ?
C3B C2B 1.420(14) . ?
C3B C4 1.352(16) . ?
C2B H2B 0.9300 . ?
C2B C1 1.378(14) . ?
C1 C6B 1.385(16) . ?
C6B H6B 0.9300 . ?
C6B C5B 1.441(13) . ?
C5B H5B 0.9300 . ?
C5B C4 1.326(14) . ?
C4 C7B 1.474(16) . ?
C7B H7B 0.9300 . ?
C7B C8B 1.28(2) . ?
C8B H8B 0.9300 . ?
C8B C9 1.492(17) . ?
C11B H11B 0.9300 . ?
C11B C10B 1.370(15) . ?
C11B C12 1.406(14) . ?
C10B H10B 0.9300 . ?
C10B C9 1.482(12) . ?
C9 C14B 1.483(14) . ?
C14B H14B 0.9300 . ?
C14B C13B 1.338(16) . ?
C13B H13B 0.9300 . ?
C13B C12 1.405(14) . ?
C15B H15D 0.9600 . ?
C15B H15E 0.9600 . ?
C15B H15F 0.9600 . ?
C16B H16D 0.9600 . ?
C16B H16E 0.9600 . ?
C16B H16F 0.9600 . ?
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
N1 C1 C6B C5B -178.9(9) . . . . ?
O1A N1 C1 C2A -176.3(9) . . . . ?
O1A N1 C1 C6A 1.1(10) . . . . ?
O2A N1 C1 C2A 3.2(11) . . . . ?
O2A N1 C1 C6A -179.3(10) . . . . ?
C2A C3A C4 C5A 1.2(11) . . . . ?
C2A C3A C4 C7A -179.8(8) . . . . ?
C3A C2A C1 N1 179.5(7) . . . . ?
C3A C2A C1 C6A 2.1(12) . . . . ?
C5A C6A C1 N1 179.6(6) . . . . ?
C5A C6A C1 C2A -3.0(11) . . . . ?
C6A C5A C4 C3A -2.2(11) . . . . ?
C6A C5A C4 C7A 179.0(8) . . . . ?
C7A C8A C9 C10A -20.0(13) . . . . ?
C7A C8A C9 C14A 161.9(8) . . . . ?
C8A C7A C4 C3A -161.0(8) . . . . ?
C8A C7A C4 C5A 17.8(14) . . . . ?
C10A C11A C12 N2 179.3(6) . . . . ?
C10A C11A C12 C13A -0.7(10) . . . . ?
C11A C10A C9 C8A -179.5(8) . . . . ?
C11A C10A C9 C14A -1.5(11) . . . . ?
C13A C14A C9 C8A -179.6(8) . . . . ?
C13A C14A C9 C10A 2.2(11) . . . . ?
C14A C13A C12 N2 -178.5(7) . . . . ?
C14A C13A C12 C11A 1.5(11) . . . . ?
C15A N2 C12 C11A 166.8(8) . . . . ?
C15A N2 C12 C13A -13.2(10) . . . . ?
C16A N2 C12 C11A 8.0(14) . . . . ?
C16A N2 C12 C13A -172.0(12) . . . . ?
O1B N1 C1 C2B 172.1(10) . . . . ?
O1B N1 C1 C6B -7.7(11) . . . . ?
O2B N1 C1 C2B 3.0(13) . . . . ?
O2B N1 C1 C6B -176.8(11) . . . . ?
C3B C2B C1 N1 178.6(9) . . . . ?
C3B C2B C1 C6B -1.7(16) . . . . ?
C3B C4 C7B C8B -80(4) . . . . ?
C2B C3B C4 C5B -4.9(17) . . . . ?
C2B C3B C4 C7B -148(2) . . . . ?
C2B C1 C6B C5B 1.4(15) . . . . ?
C1 C2A C3A C4 -1.2(12) . . . . ?
C1 C6B C5B C4 -2.9(17) . . . . ?
C6B C5B C4 C3B 4.6(17) . . . . ?
C6B C5B C4 C7B 159(2) . . . . ?
C5B C4 C7B C8B 133(3) . . . . ?
C4 C5A C6A C1 3.1(11) . . . . ?
C4 C7A C8A C9 -177.5(11) . . . . ?
C4 C3B C2B C1 3.5(18) . . . . ?
C4 C7B C8B C9 -178(4) . . . . ?
C7B C8B C9 C10B -135(4) . . . . ?
C7B C8B C9 C14B 69(6) . . . . ?
C8B C9 C14B C13B 155(3) . . . . ?
C11B C10B C9 C8B -165(2) . . . . ?
C11B C10B C9 C14B -2.4(17) . . . . ?
C10B C11B C12 N2 -179.5(11) . . . . ?
C10B C11B C12 C13B 2.3(18) . . . . ?
C10B C9 C14B C13B 1.8(17) . . . . ?
C9 C10A C11A C12 0.8(12) . . . . ?
C9 C14B C13B C12 1(2) . . . . ?
C14B C13B C12 N2 178.9(12) . . . . ?
C14B C13B C12 C11B -2.9(19) . . . . ?
C12 C13A C14A C9 -2.3(12) . . . . ?
C12 C11B C10B C9 0(2) . . . . ?
C15B N2 C12 C11B -162.6(12) . . . . ?
C15B N2 C12 C13B 15.6(13) . . . . ?
C16B N2 C12 C11B -15.0(15) . . . . ?
C16B N2 C12 C13B 163.2(14) . . . . ?
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
-0.0061 -0.9972 -5.8840 0.1178 -0.1216 -0.6062
-2.9998 -1.0027 -2.3350 0.5547 -0.6510 -0.1521
0.0061 0.9972 5.8840 -0.1178 0.1216 0.6062
2.9998 1.0027 2.3350 -0.5547 0.6510 0.1521
-0.0006 -0.9999 0.0344 0.1770 0.0973 -0.0534
0.0006 0.9999 -0.0344 -0.1770 -0.0973 0.0534
