#------------------------------------------------------------------------------
#$Date: 2021-05-05 10:59:25 +0200 (Wed 05 de May de 2021) $
#$Revision: 264937 $
#$URL: svn://www.crystallography.net/cod/cif/7/06/04/7060480.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_7060480
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         'C15 H13 N O3'
_chemical_formula_sum            'C15 H13 N O3'
_chemical_formula_weight         255.26
_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             2021-02-24
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2021-03-10 deposited with the CCDC.	2021-03-19 downloaded from the CCDC.
;
_cell_angle_alpha                109.5280(10)
_cell_angle_beta                 103.3890(10)
_cell_angle_gamma                90.9490(10)
_cell_formula_units_Z            6
_cell_length_a                   11.6720(2)
_cell_length_b                   11.8172(2)
_cell_length_c                   14.7910(2)
_cell_measurement_reflns_used    44313
_cell_measurement_temperature    120.00(10)
_cell_measurement_theta_max      76.5430
_cell_measurement_theta_min      3.2260
_cell_volume                     1860.67(5)
_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    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      120.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.1977
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.988
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     -1.00  25.00   1.00    1.00    --   38.00  95.00-153.25   26
  2  ω   -116.00 -17.00   1.00    1.00    --  -41.78 -37.00 -30.00   99
  3  ω    -66.00  33.00   1.00    1.00    --  -41.78  37.00 150.00   99
  4  ω    -34.00  74.00   1.00    1.00    --   41.78 -77.00-180.00  108
  5  ω     14.00 114.00   1.00    1.00    --   41.78  57.00 150.00  100
  6  ω     17.00 116.00   1.00    1.00    --   41.78  37.00  30.00   99
  7  ω     23.00  98.00   1.00    1.00    --   41.78-125.00  60.00   75
  8  ω     11.00  38.00   1.00    1.00    --   46.00  84.00  23.63   27
  9  ω     17.00  45.00   1.00    1.00    --   50.00  80.00 -29.30   28
 10  ω     16.00  45.00   1.00    1.00    --   50.00  82.00  98.61   29
 11  ω     16.00  45.00   1.00    1.00    --   50.00  82.00-134.05   29
 12  ω     17.00  45.00   1.00    1.00    --   50.00  80.00 -96.44   28
 13  ω     30.00 137.00   1.00    1.00    --   62.00  75.00  56.98  107
 14  ω     29.00 138.00   1.00    1.00    --   62.00  77.00 166.54  109
 15  ω     34.00 142.00   1.00    1.00    --   66.00  76.00 -21.20  108
 16  ω     34.00 142.00   1.00    1.00    --   66.00  76.00-122.58  108
 17  ω     34.00 141.00   1.00    1.00    --   66.00  75.00 -89.04  107
 18  ω     33.00 142.00   1.00    1.00    --   66.00  77.00 109.95  109
 19  ω     38.00 145.00   1.00    1.00    --   70.00  74.00 131.66  107
 20  ω     37.00 146.00   1.00    1.00    --   70.00  77.00 -59.68  109
 21  ω     41.00 150.00   1.00    1.00    --   74.00  77.00-125.49  109
 22  ω     42.00 150.00   1.00    1.00    --   74.00  76.00-164.20  108
 23  ω     47.00 151.00   1.00    3.00    --   78.00  69.00  80.42  104
 24  ω     53.00 154.00   1.00    3.00    --   82.00  62.00 119.13  101
 25  ω     52.00 155.00   1.00    3.00    --   82.00  65.00 -23.54  103
 26  ω     50.00 157.00   1.00    3.00    --   82.00  74.00   0.50  107
 27  ω     52.00 155.00   1.00    3.00    --   82.00  68.00-163.33  103
 28  ω     55.00 159.00   1.00    3.00    --   86.00  69.00 158.37  104
 29  ω     53.00 162.00   1.00    3.00    --   86.00  77.00  14.40  109
 30  ω     55.00 160.00   1.00    3.00    --   86.00  72.00-140.26  105
 31  ω     76.00 178.00   1.00    3.00    --  106.00  68.00  67.11  102
 32  ω     83.00 178.00   1.00    3.00    --  112.00  61.00   0.00   95
 33  ω     79.00 178.00   1.00    3.00    --  112.00  77.00  60.00   99
 34  ω     83.00 178.00   1.00    3.00    --  112.00  61.00 -90.00   95
 35  ω     29.00 109.00   1.00    3.00    --  112.00 -94.00  90.00   80
 36  ω     79.00 178.00   1.00    3.00    --  112.00  77.00 150.00   99
 37  ω     36.00 116.00   1.00    3.00    --  112.00-111.00-150.00   80
 38  ω     79.00 178.00   1.00    3.00    --  112.00  77.00   0.00   99
 39  ω     79.00 178.00   1.00    3.00    --  112.00  77.00 -90.00   99
 40  ω     36.00 116.00   1.00    3.00    --  112.00-111.00  60.00   80
 41  ω     79.00 178.00   1.00    3.00    --  112.00  77.00 120.00   99
 42  ω     29.00 109.00   1.00    3.00    --  112.00 -94.00 -90.00   80
 43  ω     79.00 178.00   1.00    3.00    --  112.00  77.00-150.00   99
 44  ω     79.00 178.00   1.00    3.00    --  112.00  77.00  90.00   99
 45  ω     36.00 116.00   1.00    3.00    --  112.00-111.00  30.00   80
 46  ω     40.00 141.00   1.00    3.00    --  112.00 -61.00 120.00  101
 47  ω     79.00 178.00   1.00    3.00    --  112.00  77.00 -60.00   99
 48  ω     79.00 178.00   1.00    3.00    --  112.00  77.00-120.00   99
 49  ω     83.00 178.00   1.00    3.00    --  112.00  61.00-120.00   95
 50  ω     83.00 178.00   1.00    3.00    --  112.00  61.00  90.00   95
 51  ω     79.00 178.00   1.00    3.00    --  112.00  77.00-180.00   99
 52  ω     79.00 178.00   1.00    3.00    --  112.00  77.00  30.00   99
 53  ω     29.00 109.00   1.00    3.00    --  112.00 -94.00 120.00   80
 54  ω     29.00 109.00   1.00    3.00    --  112.00 -94.00 -30.00   80
 55  ω     79.00 178.00   1.00    3.00    --  112.00  77.00 -30.00   99
 56  ω     83.00 178.00   1.00    3.00    --  112.00  61.00 150.00   95
 57  ω   -114.00 -14.00   1.00    1.00    --  -41.78 -57.00-180.00  100
 58  ω      6.00  33.00   1.00    1.00    --   42.00  88.00  71.80   27
 59  ω     16.00 119.00   1.00    1.00    --   46.00  67.00 -14.87  103
 60  ω     11.00  38.00   1.00    1.00    --   46.00  84.00 177.90   27
 61  ω     26.00 133.00   1.00    1.00    --   58.00  75.00  18.53  107
 62  ω     34.00 132.00   1.00    1.00    --   66.00  76.00  82.90   98
 63  ω     38.00 146.00   1.00    1.00    --   70.00  76.00-171.19  108
 64  ω     38.00 145.00   1.00    1.00    --   70.00  75.00   3.28  107
 65  ω     44.00 147.00   1.00    1.00    --   74.00  66.00  57.91  103
;
_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      0.1186014000
_diffrn_orient_matrix_UB_12      -0.0556060000
_diffrn_orient_matrix_UB_13      0.0117282000
_diffrn_orient_matrix_UB_21      0.0122192000
_diffrn_orient_matrix_UB_22      0.0100232000
_diffrn_orient_matrix_UB_23      -0.0986176000
_diffrn_orient_matrix_UB_31      0.0662386000
_diffrn_orient_matrix_UB_32      0.1270589000
_diffrn_orient_matrix_UB_33      0.0563507000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0297
_diffrn_reflns_av_unetI/netI     0.0128
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.988
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            72195
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.988
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         76.984
_diffrn_reflns_theta_min         3.276
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.787
_exptl_absorpt_correction_T_max  0.908
_exptl_absorpt_correction_T_min  0.871
_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            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.367
_exptl_crystal_description       block
_exptl_crystal_F_000             804
_exptl_crystal_size_max          0.253
_exptl_crystal_size_mid          0.213
_exptl_crystal_size_min          0.164
_refine_diff_density_max         0.497
_refine_diff_density_min         -0.242
_refine_diff_density_rms         0.038
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.059
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     517
_refine_ls_number_reflns         7769
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.059
_refine_ls_R_factor_all          0.0417
_refine_ls_R_factor_gt           0.0390
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0573P)²+0.5361P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1076
_refine_ls_wR_factor_ref         0.1103
_reflns_Friedel_coverage         0.000
_reflns_number_gt                7134
_reflns_number_total             7769
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d1nj00456e2.cif
_cod_data_source_block           compound_1c
_cod_depositor_comments
'Adding full bibliography for 7060468--7060480.cif.'
_cod_database_code               7060480
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C15 H13 N1 O3'
_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 99.90
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     71.98
_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.a Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C5(H5), C6(H6), C7(H7), C8(H8), C10(H10), C11(H11), C13(H13),
 C14(H14), C17(H17), C18(H18), C20(H20), C21(H21), C22(H22), C23(H23), C25(H25),
  C26(H26), C28(H28), C29(H29), C32(H32), C33(H33), C35(H35), C36(H36),
 C37(H37), C38(H38), C40(H40), C41(H41), C43(H43), C44(H44)
2.b Idealised Me refined as rotating group:
 C15(H15A,H15B,H15C), C30(H30A,H30B,H30C), C45(H45A,H45B,H45C)
;
_ins_header
;
TITL jk1903_a in P-1 
REM P-1 (#2 in standard setting)
CELL 1.54184  11.672032  11.817150  14.790987 109.5282 103.3892  90.9488
ZERR    5.00   0.000164   0.000186   0.000208   0.0014   0.0012   0.0012
LATT  1
SFAC C H N O
UNIT 75.00 65.00 5.00 15.00
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 1.358
_oxdiff_exptl_absorpt_empirical_full_min 0.803
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
O1 O 1.16751(8) 0.73065(8) 0.58984(7) 0.0375(2) Uani 1 1 d . . . . .
O2 O 1.00910(8) 0.81279(9) 0.61786(7) 0.0419(2) Uani 1 1 d . . . . .
O3 O 1.78640(8) 1.55719(8) 1.36073(6) 0.03211(19) Uani 1 1 d . . . . .
N1 N 1.11708(9) 0.80975(9) 0.63907(7) 0.0286(2) Uani 1 1 d . . . . .
C1 C 1.18841(10) 0.90451(10) 0.72737(8) 0.0251(2) Uani 1 1 d . . . . .
C2 C 1.31038(10) 0.90469(10) 0.74939(8) 0.0267(2) Uani 1 1 d . . . . .
H2 H 1.346058 0.846029 0.708559 0.032 Uiso 1 1 calc R . . . .
C3 C 1.37818(10) 0.99344(10) 0.83300(8) 0.0265(2) Uani 1 1 d . . . . .
H3 H 1.460130 0.993927 0.848530 0.032 Uiso 1 1 calc R . . . .
C4 C 1.32549(10) 1.08285(10) 0.89487(8) 0.0247(2) Uani 1 1 d . . . . .
C5 C 1.20178(10) 1.07961(11) 0.86925(8) 0.0290(2) Uani 1 1 d . . . . .
H5 H 1.165385 1.138738 0.908974 0.035 Uiso 1 1 calc R . . . .
C6 C 1.13247(10) 0.99063(11) 0.78632(9) 0.0298(2) Uani 1 1 d . . . . .
H6 H 1.050395 0.988753 0.770605 0.036 Uiso 1 1 calc R . . . .
C7 C 1.39412(10) 1.17884(10) 0.98431(8) 0.0260(2) Uani 1 1 d . . . . .
H7 H 1.351767 1.235830 1.019517 0.031 Uiso 1 1 calc R . . . .
C8 C 1.51191(10) 1.19229(10) 1.02012(8) 0.0260(2) Uani 1 1 d . . . . .
H8 H 1.553555 1.134926 0.984431 0.031 Uiso 1 1 calc R . . . .
C9 C 1.58247(10) 1.28679(10) 1.10885(8) 0.0241(2) Uani 1 1 d . . . . .
C10 C 1.70562(10) 1.28887(10) 1.13386(8) 0.0263(2) Uani 1 1 d . . . . .
H10 H 1.740738 1.229201 1.093372 0.032 Uiso 1 1 calc R . . . .
C11 C 1.77772(10) 1.37646(10) 1.21676(8) 0.0262(2) Uani 1 1 d . . . . .
H11 H 1.859491 1.375203 1.231308 0.031 Uiso 1 1 calc R . . . .
C12 C 1.72597(10) 1.46619(10) 1.27781(8) 0.0256(2) Uani 1 1 d . . . . .
C13 C 1.60299(11) 1.46513(11) 1.25492(8) 0.0297(2) Uani 1 1 d . . . . .
H13 H 1.568012 1.524316 1.295974 0.036 Uiso 1 1 calc R . . . .
C14 C 1.53272(10) 1.37769(10) 1.17242(8) 0.0277(2) Uani 1 1 d . . . . .
H14 H 1.450943 1.378812 1.158543 0.033 Uiso 1 1 calc R . . . .
C15 C 1.91287(11) 1.56102(13) 1.38723(9) 0.0379(3) Uani 1 1 d . . . . .
H15A H 1.943380 1.566347 1.333666 0.057 Uiso 1 1 calc GR . . . .
H15B H 1.935022 1.489023 1.400252 0.057 Uiso 1 1 calc GR . . . .
H15C H 1.944952 1.630250 1.445511 0.057 Uiso 1 1 calc GR . . . .
O4 O 0.12296(8) 0.29687(8) 0.07324(6) 0.0375(2) Uani 1 1 d . . . . .
O5 O 0.01468(8) 0.24875(8) 0.15814(7) 0.0389(2) Uani 1 1 d . . . . .
O6 O 0.84524(7) 1.00735(7) 0.84433(6) 0.03191(19) Uani 1 1 d . . . . .
N2 N 0.09895(8) 0.30765(9) 0.15258(7) 0.0296(2) Uani 1 1 d . . . . .
C16 C 0.17523(9) 0.39271(10) 0.24357(8) 0.0243(2) Uani 1 1 d . . . . .
C17 C 0.25248(10) 0.47770(10) 0.23611(8) 0.0261(2) Uani 1 1 d . . . . .
H17 H 0.252942 0.482450 0.174690 0.031 Uiso 1 1 calc R . . . .
C18 C 0.32858(9) 0.55500(10) 0.32151(8) 0.0257(2) Uani 1 1 d . . . . .
H18 H 0.380045 0.613019 0.317463 0.031 Uiso 1 1 calc R . . . .
C19 C 0.32967(9) 0.54755(10) 0.41482(8) 0.0241(2) Uani 1 1 d . . . . .
C20 C 0.24760(10) 0.46273(10) 0.41882(8) 0.0257(2) Uani 1 1 d . . . . .
H20 H 0.245195 0.458515 0.480033 0.031 Uiso 1 1 calc R . . . .
C21 C 0.16996(10) 0.38502(10) 0.33397(8) 0.0260(2) Uani 1 1 d . . . . .
H21 H 0.115711 0.329129 0.337543 0.031 Uiso 1 1 calc R . . . .
C22 C 0.41237(10) 0.62409(10) 0.50661(8) 0.0256(2) Uani 1 1 d . . . . .
H22 H 0.398820 0.622929 0.565845 0.031 Uiso 1 1 calc R . . . .
C23 C 0.50587(10) 0.69564(10) 0.51263(8) 0.0255(2) Uani 1 1 d . . . . .
H23 H 0.518406 0.695745 0.452815 0.031 Uiso 1 1 calc R . . . .
C24 C 0.59066(9) 0.77375(9) 0.60250(8) 0.0241(2) Uani 1 1 d . . . . .
C25 C 0.68385(10) 0.84119(10) 0.59242(8) 0.0267(2) Uani 1 1 d . . . . .
H25 H 0.689969 0.834198 0.529231 0.032 Uiso 1 1 calc R . . . .
C26 C 0.76666(10) 0.91760(10) 0.67367(8) 0.0267(2) Uani 1 1 d . . . . .
H26 H 0.827361 0.961575 0.664857 0.032 Uiso 1 1 calc R . . . .
C27 C 0.75944(10) 0.92892(10) 0.76888(8) 0.0252(2) Uani 1 1 d . . . . .
C28 C 0.66844(10) 0.86180(10) 0.78136(8) 0.0271(2) Uani 1 1 d . . . . .
H28 H 0.663250 0.868099 0.844630 0.032 Uiso 1 1 calc R . . . .
C29 C 0.58570(9) 0.78552(10) 0.69845(8) 0.0261(2) Uani 1 1 d . . . . .
H29 H 0.525342 0.741087 0.707250 0.031 Uiso 1 1 calc R . . . .
C30 C 0.84282(12) 1.01865(12) 0.94320(9) 0.0375(3) Uani 1 1 d . . . . .
H30A H 0.853819 0.942305 0.951973 0.056 Uiso 1 1 calc GR . . . .
H30B H 0.767856 1.043223 0.954487 0.056 Uiso 1 1 calc GR . . . .
H30C H 0.905179 1.077992 0.989485 0.056 Uiso 1 1 calc GR . . . .
O7 O -0.01041(8) 0.53654(9) 0.14308(7) 0.0388(2) Uani 1 1 d . . . . .
O8 O -0.14757(9) 0.65658(9) 0.16146(7) 0.0443(2) Uani 1 1 d . . . . .
O9 O -0.88468(7) -0.10681(7) -0.57177(6) 0.02994(18) Uani 1 1 d . . . . .
N3 N -0.11138(9) 0.56225(9) 0.11678(7) 0.0290(2) Uani 1 1 d . . . . .
C31 C -0.19277(10) 0.47610(10) 0.02957(8) 0.0253(2) Uani 1 1 d . . . . .
C32 C -0.31032(10) 0.49833(11) 0.00527(9) 0.0285(2) Uani 1 1 d . . . . .
H32 H -0.336455 0.568721 0.042171 0.034 Uiso 1 1 calc R . . . .
C33 C -0.38780(10) 0.41305(11) -0.07533(9) 0.0305(2) Uani 1 1 d . . . . .
H33 H -0.466976 0.426387 -0.091934 0.037 Uiso 1 1 calc R . . . .
C34 C -0.34939(11) 0.30694(11) -0.13248(8) 0.0287(2) Uani 1 1 d . . . . .
C35 C -0.22999(11) 0.28969(11) -0.10596(8) 0.0297(2) Uani 1 1 d . . . . .
H35 H -0.202580 0.220645 -0.143541 0.036 Uiso 1 1 calc R . . . .
C36 C -0.15149(10) 0.37278(11) -0.02517(8) 0.0284(2) Uani 1 1 d . . . . .
H36 H -0.072373 0.359537 -0.007870 0.034 Uiso 1 1 calc R . . . .
C37 C -0.42831(11) 0.21473(11) -0.21877(9) 0.0298(2) Uani 1 1 d . . . . .
H37 H -0.395072 0.147694 -0.252737 0.036 Uiso 1 1 calc R . . . .
C38 C -0.54399(11) 0.21950(11) -0.25233(9) 0.0299(2) Uani 1 1 d . . . . .
H38 H -0.575773 0.287242 -0.217667 0.036 Uiso 1 1 calc R . . . .
C39 C -0.62626(10) 0.13035(10) -0.33731(8) 0.0274(2) Uani 1 1 d . . . . .
C40 C -0.74597(11) 0.15019(10) -0.35618(8) 0.0284(2) Uani 1 1 d . . . . .
H40 H -0.769602 0.219409 -0.315290 0.034 Uiso 1 1 calc R . . . .
C41 C -0.82962(10) 0.06968(10) -0.43384(8) 0.0278(2) Uani 1 1 d . . . . .
H41 H -0.908659 0.084814 -0.444973 0.033 Uiso 1 1 calc R . . . .
C42 C -0.79553(10) -0.03462(10) -0.49576(8) 0.0241(2) Uani 1 1 d . . . . .
C43 C -0.67709(10) -0.05720(10) -0.47859(8) 0.0269(2) Uani 1 1 d . . . . .
H43 H -0.653996 -0.126878 -0.519348 0.032 Uiso 1 1 calc R . . . .
C44 C -0.59383(10) 0.02505(11) -0.40021(9) 0.0287(2) Uani 1 1 d . . . . .
H44 H -0.514791 0.009920 -0.389224 0.034 Uiso 1 1 calc R . . . .
C45 C -0.85585(12) -0.21672(11) -0.63581(9) 0.0350(3) Uani 1 1 d . . . . .
H45A H -0.925452 -0.257984 -0.686611 0.052 Uiso 1 1 calc GR . . . .
H45B H -0.826381 -0.267037 -0.598148 0.052 Uiso 1 1 calc GR . . . .
H45C H -0.796326 -0.199071 -0.665741 0.052 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
-5 -5 4 0.1564
-3 -1 5 0.1148
5 5 -4 0.0564
1 -2 -5 0.1515
-1 2 5 0.0805
5 -4 4 0.0724
3 1 -5 0.1148
-5 4 -4 0.0914
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
C12 O3 C15 117.54(9) . . ?
O1 N1 O2 123.08(10) . . ?
O1 N1 C1 118.65(10) . . ?
O2 N1 C1 118.27(10) . . ?
C2 C1 N1 118.62(10) . . ?
C6 C1 N1 119.32(10) . . ?
C6 C1 C2 122.06(10) . . ?
C1 C2 H2 120.5 . . ?
C3 C2 C1 118.91(10) . . ?
C3 C2 H2 120.5 . . ?
C2 C3 H3 119.5 . . ?
C2 C3 C4 121.10(10) . . ?
C4 C3 H3 119.5 . . ?
C3 C4 C7 122.90(10) . . ?
C5 C4 C3 118.00(10) . . ?
C5 C4 C7 119.10(10) . . ?
C4 C5 H5 119.2 . . ?
C6 C5 C4 121.65(11) . . ?
C6 C5 H5 119.2 . . ?
C1 C6 H6 120.9 . . ?
C5 C6 C1 118.29(11) . . ?
C5 C6 H6 120.9 . . ?
C4 C7 H7 116.9 . . ?
C8 C7 C4 126.29(11) . . ?
C8 C7 H7 116.9 . . ?
C7 C8 H8 116.3 . . ?
C7 C8 C9 127.45(11) . . ?
C9 C8 H8 116.3 . . ?
C10 C9 C8 119.77(10) . . ?
C10 C9 C14 116.96(10) . . ?
C14 C9 C8 123.27(10) . . ?
C9 C10 H10 118.7 . . ?
C11 C10 C9 122.63(10) . . ?
C11 C10 H10 118.7 . . ?
C10 C11 H11 120.4 . . ?
C10 C11 C12 119.11(10) . . ?
C12 C11 H11 120.4 . . ?
O3 C12 C11 124.94(11) . . ?
O3 C12 C13 115.78(10) . . ?
C11 C12 C13 119.27(10) . . ?
C12 C13 H13 119.5 . . ?
C14 C13 C12 120.91(10) . . ?
C14 C13 H13 119.5 . . ?
C9 C14 H14 119.4 . . ?
C13 C14 C9 121.11(11) . . ?
C13 C14 H14 119.4 . . ?
O3 C15 H15A 109.5 . . ?
O3 C15 H15B 109.5 . . ?
O3 C15 H15C 109.5 . . ?
H15A C15 H15B 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C27 O6 C30 117.12(9) . . ?
O4 N2 C16 118.33(10) . . ?
O5 N2 O4 122.88(10) . . ?
O5 N2 C16 118.78(10) . . ?
C17 C16 N2 118.38(10) . . ?
C21 C16 N2 119.38(10) . . ?
C21 C16 C17 122.23(10) . . ?
C16 C17 H17 120.6 . . ?
C18 C17 C16 118.73(10) . . ?
C18 C17 H17 120.6 . . ?
C17 C18 H18 119.5 . . ?
C17 C18 C19 121.09(10) . . ?
C19 C18 H18 119.5 . . ?
C18 C19 C22 122.87(10) . . ?
C20 C19 C18 118.02(10) . . ?
C20 C19 C22 119.12(10) . . ?
C19 C20 H20 119.2 . . ?
C21 C20 C19 121.65(10) . . ?
C21 C20 H20 119.2 . . ?
C16 C21 H21 120.9 . . ?
C20 C21 C16 118.21(10) . . ?
C20 C21 H21 120.9 . . ?
C19 C22 H22 117.2 . . ?
C23 C22 C19 125.52(10) . . ?
C23 C22 H22 117.2 . . ?
C22 C23 H23 116.3 . . ?
C22 C23 C24 127.44(10) . . ?
C24 C23 H23 116.3 . . ?
C25 C24 C23 118.40(10) . . ?
C29 C24 C23 124.31(10) . . ?
C29 C24 C25 117.29(10) . . ?
C24 C25 H25 119.1 . . ?
C26 C25 C24 121.77(10) . . ?
C26 C25 H25 119.1 . . ?
C25 C26 H26 120.0 . . ?
C25 C26 C27 120.02(10) . . ?
C27 C26 H26 120.0 . . ?
O6 C27 C26 115.51(10) . . ?
O6 C27 C28 124.92(10) . . ?
C26 C27 C28 119.57(10) . . ?
C27 C28 H28 120.3 . . ?
C29 C28 C27 119.49(10) . . ?
C29 C28 H28 120.3 . . ?
C24 C29 H29 119.1 . . ?
C28 C29 C24 121.86(10) . . ?
C28 C29 H29 119.1 . . ?
O6 C30 H30A 109.5 . . ?
O6 C30 H30B 109.5 . . ?
O6 C30 H30C 109.5 . . ?
H30A C30 H30B 109.5 . . ?
H30A C30 H30C 109.5 . . ?
H30B C30 H30C 109.5 . . ?
C42 O9 C45 117.74(9) . . ?
O7 N3 C31 118.61(9) . . ?
O8 N3 O7 123.03(10) . . ?
O8 N3 C31 118.36(10) . . ?
C32 C31 N3 119.05(10) . . ?
C36 C31 N3 119.12(10) . . ?
C36 C31 C32 121.81(11) . . ?
C31 C32 H32 120.8 . . ?
C33 C32 C31 118.39(11) . . ?
C33 C32 H32 120.8 . . ?
C32 C33 H33 119.3 . . ?
C32 C33 C34 121.48(11) . . ?
C34 C33 H33 119.3 . . ?
C33 C34 C37 123.23(11) . . ?
C35 C34 C33 117.93(11) . . ?
C35 C34 C37 118.84(11) . . ?
C34 C35 H35 119.2 . . ?
C36 C35 C34 121.57(11) . . ?
C36 C35 H35 119.2 . . ?
C31 C36 H36 120.6 . . ?
C35 C36 C31 118.81(11) . . ?
C35 C36 H36 120.6 . . ?
C34 C37 H37 117.4 . . ?
C38 C37 C34 125.20(11) . . ?
C38 C37 H37 117.4 . . ?
C37 C38 H38 116.3 . . ?
C37 C38 C39 127.37(11) . . ?
C39 C38 H38 116.3 . . ?
C40 C39 C38 117.89(10) . . ?
C40 C39 C44 117.69(10) . . ?
C44 C39 C38 124.41(11) . . ?
C39 C40 H40 119.2 . . ?
C41 C40 C39 121.60(10) . . ?
C41 C40 H40 119.2 . . ?
C40 C41 H41 120.1 . . ?
C40 C41 C42 119.86(10) . . ?
C42 C41 H41 120.1 . . ?
O9 C42 C41 115.18(10) . . ?
O9 C42 C43 124.91(10) . . ?
C43 C42 C41 119.90(10) . . ?
C42 C43 H43 120.2 . . ?
C44 C43 C42 119.53(10) . . ?
C44 C43 H43 120.2 . . ?
C39 C44 H44 119.3 . . ?
C43 C44 C39 121.43(10) . . ?
C43 C44 H44 119.3 . . ?
O9 C45 H45A 109.5 . . ?
O9 C45 H45B 109.5 . . ?
O9 C45 H45C 109.5 . . ?
H45A C45 H45B 109.5 . . ?
H45A C45 H45C 109.5 . . ?
H45B C45 H45C 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 N1 1.2297(13) . ?
O2 N1 1.2305(13) . ?
O3 C12 1.3604(13) . ?
O3 C15 1.4327(16) . ?
N1 C1 1.4631(14) . ?
C1 C2 1.3848(16) . ?
C1 C6 1.3837(16) . ?
C2 H2 0.9300 . ?
C2 C3 1.3811(16) . ?
C3 H3 0.9300 . ?
C3 C4 1.4029(16) . ?
C4 C5 1.4018(16) . ?
C4 C7 1.4678(15) . ?
C5 H5 0.9300 . ?
C5 C6 1.3837(16) . ?
C6 H6 0.9300 . ?
C7 H7 0.9300 . ?
C7 C8 1.3399(16) . ?
C8 H8 0.9300 . ?
C8 C9 1.4618(15) . ?
C9 C10 1.3964(16) . ?
C9 C14 1.4048(16) . ?
C10 H10 0.9300 . ?
C10 C11 1.3885(16) . ?
C11 H11 0.9300 . ?
C11 C12 1.3923(16) . ?
C12 C13 1.3952(17) . ?
C13 H13 0.9300 . ?
C13 C14 1.3765(16) . ?
C14 H14 0.9300 . ?
C15 H15A 0.9600 . ?
C15 H15B 0.9600 . ?
C15 H15C 0.9600 . ?
O4 N2 1.2351(13) . ?
O5 N2 1.2295(14) . ?
O6 C27 1.3666(13) . ?
O6 C30 1.4303(15) . ?
N2 C16 1.4578(14) . ?
C16 C17 1.3872(16) . ?
C16 C21 1.3853(15) . ?
C17 H17 0.9300 . ?
C17 C18 1.3787(16) . ?
C18 H18 0.9300 . ?
C18 C19 1.4093(15) . ?
C19 C20 1.3999(15) . ?
C19 C22 1.4617(15) . ?
C20 H20 0.9300 . ?
C20 C21 1.3837(15) . ?
C21 H21 0.9300 . ?
C22 H22 0.9300 . ?
C22 C23 1.3371(16) . ?
C23 H23 0.9300 . ?
C23 C24 1.4625(15) . ?
C24 C25 1.4022(15) . ?
C24 C29 1.3939(15) . ?
C25 H25 0.9300 . ?
C25 C26 1.3790(15) . ?
C26 H26 0.9300 . ?
C26 C27 1.3919(15) . ?
C27 C28 1.3972(16) . ?
C28 H28 0.9300 . ?
C28 C29 1.3901(16) . ?
C29 H29 0.9300 . ?
C30 H30A 0.9600 . ?
C30 H30B 0.9600 . ?
C30 H30C 0.9600 . ?
O7 N3 1.2293(13) . ?
O8 N3 1.2289(14) . ?
O9 C42 1.3646(13) . ?
O9 C45 1.4272(14) . ?
N3 C31 1.4579(14) . ?
C31 C32 1.3883(16) . ?
C31 C36 1.3847(16) . ?
C32 H32 0.9300 . ?
C32 C33 1.3864(17) . ?
C33 H33 0.9300 . ?
C33 C34 1.4047(17) . ?
C34 C35 1.3955(17) . ?
C34 C37 1.4688(16) . ?
C35 H35 0.9300 . ?
C35 C36 1.3821(16) . ?
C36 H36 0.9300 . ?
C37 H37 0.9300 . ?
C37 C38 1.3355(17) . ?
C38 H38 0.9300 . ?
C38 C39 1.4609(16) . ?
C39 C40 1.3997(16) . ?
C39 C44 1.4007(16) . ?
C40 H40 0.9300 . ?
C40 C41 1.3773(16) . ?
C41 H41 0.9300 . ?
C41 C42 1.3953(15) . ?
C42 C43 1.3935(15) . ?
C43 H43 0.9300 . ?
C43 C44 1.3881(16) . ?
C44 H44 0.9300 . ?
C45 H45A 0.9600 . ?
C45 H45B 0.9600 . ?
C45 H45C 0.9600 . ?
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
C11 H11 O5 0.93 2.57 3.3246(15) 138.6 1_766 yes
C20 H20 O3 0.93 2.53 3.4575(14) 173.6 2_777 yes
C21 H21 O2 0.93 2.54 3.4613(15) 168.8 2_666 yes
C35 H35 O6 0.93 2.55 3.3466(15) 144.3 1_444 yes
C41 H41 O9 0.93 2.49 3.3870(14) 162.0 2_354 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 N1 C1 C2 3.06(15) . . . . ?
O1 N1 C1 C6 -176.74(10) . . . . ?
O2 N1 C1 C2 -177.27(10) . . . . ?
O2 N1 C1 C6 2.92(15) . . . . ?
O3 C12 C13 C14 179.63(10) . . . . ?
N1 C1 C2 C3 -179.59(9) . . . . ?
N1 C1 C6 C5 -179.77(9) . . . . ?
C1 C2 C3 C4 -0.38(16) . . . . ?
C2 C1 C6 C5 0.43(17) . . . . ?
C2 C3 C4 C5 -0.10(16) . . . . ?
C2 C3 C4 C7 -179.93(10) . . . . ?
C3 C4 C5 C6 0.77(16) . . . . ?
C3 C4 C7 C8 -2.18(17) . . . . ?
C4 C5 C6 C1 -0.93(17) . . . . ?
C4 C7 C8 C9 -179.98(10) . . . . ?
C5 C4 C7 C8 177.99(11) . . . . ?
C6 C1 C2 C3 0.21(17) . . . . ?
C7 C4 C5 C6 -179.39(10) . . . . ?
C7 C8 C9 C10 -178.21(11) . . . . ?
C7 C8 C9 C14 2.10(18) . . . . ?
C8 C9 C10 C11 179.64(10) . . . . ?
C8 C9 C14 C13 -179.69(10) . . . . ?
C9 C10 C11 C12 -0.02(16) . . . . ?
C10 C9 C14 C13 0.61(16) . . . . ?
C10 C11 C12 O3 -179.72(10) . . . . ?
C10 C11 C12 C13 0.76(16) . . . . ?
C11 C12 C13 C14 -0.81(17) . . . . ?
C12 C13 C14 C9 0.11(17) . . . . ?
C14 C9 C10 C11 -0.66(16) . . . . ?
C15 O3 C12 C11 0.03(16) . . . . ?
C15 O3 C12 C13 179.57(10) . . . . ?
O4 N2 C16 C17 15.39(14) . . . . ?
O4 N2 C16 C21 -163.50(10) . . . . ?
O5 N2 C16 C17 -165.56(10) . . . . ?
O5 N2 C16 C21 15.56(15) . . . . ?
O6 C27 C28 C29 179.50(10) . . . . ?
N2 C16 C17 C18 -177.18(9) . . . . ?
N2 C16 C21 C20 176.70(9) . . . . ?
C16 C17 C18 C19 0.83(16) . . . . ?
C17 C16 C21 C20 -2.14(16) . . . . ?
C17 C18 C19 C20 -2.72(16) . . . . ?
C17 C18 C19 C22 177.23(10) . . . . ?
C18 C19 C20 C21 2.24(16) . . . . ?
C18 C19 C22 C23 -10.39(17) . . . . ?
C19 C20 C21 C16 0.12(16) . . . . ?
C19 C22 C23 C24 179.87(10) . . . . ?
C20 C19 C22 C23 169.56(11) . . . . ?
C21 C16 C17 C18 1.68(16) . . . . ?
C22 C19 C20 C21 -177.71(10) . . . . ?
C22 C23 C24 C25 179.40(11) . . . . ?
C22 C23 C24 C29 -0.23(18) . . . . ?
C23 C24 C25 C26 179.43(10) . . . . ?
C23 C24 C29 C28 -179.61(10) . . . . ?
C24 C25 C26 C27 0.31(17) . . . . ?
C25 C24 C29 C28 0.75(16) . . . . ?
C25 C26 C27 O6 -179.64(10) . . . . ?
C25 C26 C27 C28 0.47(16) . . . . ?
C26 C27 C28 C29 -0.63(16) . . . . ?
C27 C28 C29 C24 0.00(16) . . . . ?
C29 C24 C25 C26 -0.91(16) . . . . ?
C30 O6 C27 C26 -178.16(10) . . . . ?
C30 O6 C27 C28 1.72(16) . . . . ?
O7 N3 C31 C32 173.31(10) . . . . ?
O7 N3 C31 C36 -4.93(15) . . . . ?
O8 N3 C31 C32 -5.66(15) . . . . ?
O8 N3 C31 C36 176.10(10) . . . . ?
O9 C42 C43 C44 178.14(10) . . . . ?
N3 C31 C32 C33 -177.23(9) . . . . ?
N3 C31 C36 C35 178.01(9) . . . . ?
C31 C32 C33 C34 -0.74(17) . . . . ?
C32 C31 C36 C35 -0.18(16) . . . . ?
C32 C33 C34 C35 -0.24(16) . . . . ?
C32 C33 C34 C37 -179.58(10) . . . . ?
C33 C34 C35 C36 1.06(16) . . . . ?
C33 C34 C37 C38 -0.71(18) . . . . ?
C34 C35 C36 C31 -0.86(16) . . . . ?
C34 C37 C38 C39 -179.79(10) . . . . ?
C35 C34 C37 C38 179.96(11) . . . . ?
C36 C31 C32 C33 0.96(16) . . . . ?
C37 C34 C35 C36 -179.57(10) . . . . ?
C37 C38 C39 C40 176.42(11) . . . . ?
C37 C38 C39 C44 -2.32(19) . . . . ?
C38 C39 C40 C41 -178.98(10) . . . . ?
C38 C39 C44 C43 178.67(10) . . . . ?
C39 C40 C41 C42 0.06(17) . . . . ?
C40 C39 C44 C43 -0.08(16) . . . . ?
C40 C41 C42 O9 -178.49(9) . . . . ?
C40 C41 C42 C43 0.25(16) . . . . ?
C41 C42 C43 C44 -0.47(16) . . . . ?
C42 C43 C44 C39 0.39(17) . . . . ?
C44 C39 C40 C41 -0.15(16) . . . . ?
C45 O9 C42 C41 -178.10(10) . . . . ?
C45 O9 C42 C43 3.22(15) . . . . ?
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
-5.0039 -4.9975 3.9998 -0.2687 -0.5057 -0.7410
-2.9999 -0.9985 4.9996 -0.2416 -0.5397 -0.0438
5.0039 4.9975 -3.9998 0.2687 0.5057 0.7410
0.9969 -2.0005 -4.9994 0.1708 0.4852 -0.4699
-0.9969 2.0005 4.9994 -0.1708 -0.4852 0.4699
5.0006 -3.9991 3.9997 0.8624 -0.3734 0.0485
2.9999 0.9985 -4.9996 0.2416 0.5397 0.0438
-5.0006 3.9991 -3.9997 -0.8624 0.3734 -0.0485
