#------------------------------------------------------------------------------
#$Date: 2023-10-06 02:53:23 +0300 (Fri, 06 Oct 2023) $
#$Revision: 286720 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/56/96/1569665.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_1569665
loop_
_publ_author_name
'Borrel, Julien'
'Waser, Jerome'
_publ_section_title
;
 Azido-alkynylation of alkenes through radical-polar crossover.
;
_journal_issue                   35
_journal_name_full               'Chemical science'
_journal_page_first              9452
_journal_page_last               9460
_journal_paper_doi               10.1039/d3sc03309k
_journal_volume                  14
_journal_year                    2023
_chemical_formula_moiety         'C18 H16 N4 O'
_chemical_formula_sum            'C18 H16 N4 O'
_chemical_formula_weight         304.35
_chemical_name_systematic
N-(4-(1-Azido-4-phenylbut-3-yn-2-yl)phenyl)acetamide
_space_group_crystal_system      orthorhombic
_space_group_IT_number           56
_space_group_name_Hall           '-P 2ab 2ac'
_space_group_name_H-M_alt        'P c c n'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_audit_creation_date             2022-10-31
_audit_creation_method
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_audit_update_record
;
2023-05-19 deposited with the CCDC.	2023-08-10 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   43.729(2)
_cell_length_b                   9.4992(4)
_cell_length_c                   7.5184(3)
_cell_measurement_reflns_used    3508
_cell_measurement_temperature    140.00(10)
_cell_measurement_theta_max      70.4070
_cell_measurement_theta_min      4.0300
_cell_volume                     3123.1(2)
_computing_cell_refinement       'CrysAlisPro 1.171.42.72a (Rigaku OD, 2022)'
_computing_data_collection       'CrysAlisPro 1.171.42.72a (Rigaku OD, 2022)'
_computing_data_reduction        'CrysAlisPro 1.171.42.72a (Rigaku OD, 2022)'
_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      140.00(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            'HyPix-Arc 150'
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.953
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω   -104.00 -73.00   0.50    2.32    --  -67.15   0.00  90.00   62
  2  ω   -102.00 -76.00   0.50    2.32    --  -69.26   0.00 150.00   52
  3  ω    -98.00 -73.00   0.50    2.32    --  -69.26   0.00  30.00   50
  4  ω   -102.00 -72.00   0.50    2.32    --  -67.15   0.00 -60.00   60
  5  ω   -103.00 -73.00   0.50    2.32    --  -67.15   0.00-120.00   60
  6  ω     40.00  75.00   0.50    2.32    --   78.01 -95.00 -90.00   70
  7  ω     34.00  78.00   0.50    2.32    --   69.47 -95.00-150.00   88
  8  ω     28.00  53.00   0.50    2.32    --   66.10 -95.00-180.00   50
  9  ω     28.00  53.00   0.50    2.32    --   66.10 -95.00  30.00   50
 10  ω     34.00  60.00   0.50    2.32    --   69.47-125.00 150.00   52
 11  ω     68.00  94.00   0.50    2.32    --   69.47-125.00 150.00   52
 12  ω     57.00  85.00   0.50    2.32    --   78.01 -95.00 150.00   56
 13  ω     49.00 107.00   0.50    2.32    --   78.01  15.00 120.00  116
 14  ω     84.00 110.00   0.50    2.32    --   78.01  15.00  30.00   52
 15  ω     49.00  74.00   0.50    2.32    --   78.01  15.00  30.00   50
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy R, DW system, HyPix-Arc 150'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0055194000
_diffrn_orient_matrix_UB_12      0.1407976000
_diffrn_orient_matrix_UB_13      0.0964596000
_diffrn_orient_matrix_UB_21      0.0319615000
_diffrn_orient_matrix_UB_22      -0.0100438000
_diffrn_orient_matrix_UB_23      0.0851931000
_diffrn_orient_matrix_UB_31      0.0137741000
_diffrn_orient_matrix_UB_32      0.0799470000
_diffrn_orient_matrix_UB_33      -0.1593125000
_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  0.0431
_diffrn_reflns_av_unetI/netI     0.0462
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.953
_diffrn_reflns_limit_h_max       53
_diffrn_reflns_limit_h_min       -51
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       7
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            11322
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.953
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         74.799
_diffrn_reflns_theta_min         4.044
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.672
_exptl_absorpt_correction_T_max  0.966
_exptl_absorpt_correction_T_min  0.890
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.42.72a (Rigaku Oxford Diffraction, 2022)
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            'clear pale colourless'
_exptl_crystal_density_diffrn    1.295
_exptl_crystal_description       plate
_exptl_crystal_F_000             1280
_exptl_crystal_recrystallization_method 'Slow evaporation'
_exptl_crystal_size_max          0.241
_exptl_crystal_size_mid          0.198
_exptl_crystal_size_min          0.067
_refine_diff_density_max         0.223
_refine_diff_density_min         -0.196
_refine_diff_density_rms         0.049
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.041
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     250
_refine_ls_number_reflns         3060
_refine_ls_number_restraints     122
_refine_ls_restrained_S_all      1.040
_refine_ls_R_factor_all          0.0855
_refine_ls_R_factor_gt           0.0552
_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)+(0.0691P)²+1.1968P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1309
_refine_ls_wR_factor_ref         0.1460
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2117
_reflns_number_total             3060
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d3sc03309k2.cif
_cod_data_source_block           jb03-227
_cod_depositor_comments
'Adding full bibliography for 1569664--1569665.cif.'
_cod_original_cell_volume        3123.1(3)
_cod_database_code               1569665
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C18 H16 N4 O1'
_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   0.956
_shelx_estimated_absorpt_t_min   0.855
_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. Restrained distances
 C3-C1 \\sim C2-C1
 with sigma of 0.01
 N5-N4 \\sim N6-N5 \\sim N2-N1 \\sim N3-N2
 with sigma of 0.02
 N1-C2 \\sim N4-C3
 with sigma of 0.02
3. Uiso/Uaniso restraints and constraints
N1 \\sim N2 \\sim N3 \\sim N4 \\sim N5 \\sim N6 \\sim C1 \\sim C2 \\sim C3:
within 2A with sigma of 0.01 and sigma for terminal atoms of 0.02 within 2A
4. Others
 Sof(N4)=Sof(N5)=Sof(N6)=Sof(H1B)=Sof(C3)=Sof(H3A)=Sof(H3B)=1-FVAR(1)
 Sof(N1)=Sof(N2)=Sof(N3)=Sof(H1A)=Sof(C2)=Sof(H2A)=Sof(H2B)=FVAR(1)
5.a Ternary CH refined with riding coordinates:
 C1(H1A), C1(H1B)
5.b Secondary CH2 refined with riding coordinates:
 C2(H2A,H2B), C3(H3A,H3B)
5.c Aromatic/amide H refined with riding coordinates:
 C5(H5), C6(H6), C8(H8), C9(H9), C15(H15), C16(H16), C17(H17), C18(H18),
 C19(H19)
5.d Idealised Me refined as rotating group:
 C11(H11A,H11B,H11C)
;
_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 1.988
_oxdiff_exptl_absorpt_empirical_full_min 0.536
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y+1/2, z'
'-x, y+1/2, -z+1/2'
'x+1/2, -y, -z+1/2'
'-x, -y, -z'
'x-1/2, y-1/2, -z'
'x, -y-1/2, z-1/2'
'-x-1/2, y, z-1/2'
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 0.50853(3) 0.23508(15) 0.3436(2) 0.0363(4) Uani 1 1 d . . . . .
N1 N 0.37306(7) 0.4605(3) 0.8318(4) 0.0475(9) Uani 0.736(4) 1 d D U P A 1
N2 N 0.37979(7) 0.5685(4) 0.9106(5) 0.0445(8) Uani 0.736(4) 1 d D U P A 1
N3 N 0.3873(3) 0.6609(10) 0.9977(10) 0.0621(16) Uani 0.736(4) 1 d D U P A 1
N4 N 0.3597(2) 0.5699(10) 0.6992(12) 0.0511(19) Uani 0.264(4) 1 d D U P A 2
N5 N 0.3719(2) 0.6172(11) 0.8273(14) 0.0515(19) Uani 0.264(4) 1 d D U P A 2
N6 N 0.3839(8) 0.670(3) 0.947(3) 0.067(5) Uani 0.264(4) 1 d D U P A 2
N7 N 0.48687(4) 0.44901(19) 0.2952(2) 0.0288(4) Uani 1 1 d . . . . .
H7 H 0.4893(5) 0.531(3) 0.256(3) 0.037(7) Uiso 1 1 d . . . . .
C1 C 0.36289(5) 0.3727(3) 0.5252(3) 0.0403(6) Uani 1 1 d D U . . .
H1A H 0.359676 0.275063 0.571164 0.048 Uiso 0.736(4) 1 calc R U P A 1
H1B H 0.361535 0.267862 0.533483 0.048 Uiso 0.264(4) 1 calc R U P A 2
C2 C 0.35377(9) 0.4827(5) 0.6712(5) 0.0448(10) Uani 0.736(4) 1 d D U P A 1
H2A H 0.356806 0.579338 0.625151 0.054 Uiso 0.736(4) 1 calc R U P A 1
H2B H 0.331912 0.471347 0.702391 0.054 Uiso 0.736(4) 1 calc R U P A 1
C3 C 0.3557(3) 0.4149(12) 0.7153(11) 0.049(2) Uani 0.264(4) 1 d D U P A 2
H3A H 0.334545 0.389355 0.749443 0.059 Uiso 0.264(4) 1 calc R U P A 2
H3B H 0.370300 0.373136 0.800970 0.059 Uiso 0.264(4) 1 calc R U P A 2
C4 C 0.39603(5) 0.3918(2) 0.4684(3) 0.0334(5) Uani 1 1 d . . . . .
C5 C 0.40462(5) 0.5047(2) 0.3621(3) 0.0348(5) Uani 1 1 d . . . . .
H5 H 0.389651 0.571453 0.326341 0.042 Uiso 1 1 calc R U . . .
C6 C 0.43453(5) 0.5216(2) 0.3075(3) 0.0318(5) Uani 1 1 d . . . . .
H6 H 0.439903 0.599594 0.234910 0.038 Uiso 1 1 calc R U . . .
C7 C 0.45687(5) 0.4253(2) 0.3580(3) 0.0274(5) Uani 1 1 d . . . . .
C8 C 0.44869(5) 0.3132(2) 0.4687(3) 0.0304(5) Uani 1 1 d . . . . .
H8 H 0.463701 0.247964 0.507971 0.037 Uiso 1 1 calc R U . . .
C9 C 0.41847(5) 0.2982(2) 0.5205(3) 0.0328(5) Uani 1 1 d . . . . .
H9 H 0.413003 0.221031 0.594259 0.039 Uiso 1 1 calc R U . . .
C10 C 0.51037(5) 0.3570(2) 0.2882(3) 0.0290(5) Uani 1 1 d . . . . .
C11 C 0.53936(5) 0.4126(2) 0.2090(3) 0.0360(5) Uani 1 1 d . . . . .
H11A H 0.556052 0.402255 0.294985 0.054 Uiso 1 1 calc R U . . .
H11B H 0.536753 0.512342 0.179394 0.054 Uiso 1 1 calc R U . . .
H11C H 0.544244 0.359603 0.100856 0.054 Uiso 1 1 calc R U . . .
C12 C 0.34162(5) 0.4012(3) 0.3784(3) 0.0389(6) Uani 1 1 d . . . . .
C13 C 0.32544(5) 0.4334(3) 0.2570(3) 0.0401(6) Uani 1 1 d . . . . .
C14 C 0.30670(5) 0.4783(3) 0.1102(3) 0.0368(5) Uani 1 1 d . . . . .
C15 C 0.28813(6) 0.3847(3) 0.0179(3) 0.0442(6) Uani 1 1 d . . . . .
H15 H 0.287690 0.288107 0.050384 0.053 Uiso 1 1 calc R U . . .
C16 C 0.27018(6) 0.4330(3) -0.1225(3) 0.0506(7) Uani 1 1 d . . . . .
H16 H 0.257625 0.368729 -0.186127 0.061 Uiso 1 1 calc R U . . .
C17 C 0.27049(6) 0.5726(3) -0.1697(4) 0.0533(7) Uani 1 1 d . . . . .
H17 H 0.258126 0.604808 -0.265281 0.064 Uiso 1 1 calc R U . . .
C18 C 0.28884(6) 0.6665(3) -0.0777(4) 0.0505(7) Uani 1 1 d . . . . .
H18 H 0.288940 0.763327 -0.109477 0.061 Uiso 1 1 calc R U . . .
C19 C 0.30692(6) 0.6196(3) 0.0598(3) 0.0432(6) Uani 1 1 d . . . . .
H19 H 0.319725 0.684229 0.121069 0.052 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
1 -1 0 0.0961
2 0 -1 0.0885
-2 0 1 0.0868
1 2 0 0.1353
1 -2 -1 0.1055
-1 2 1 0.1263
1 1 0 0.1315
1 -1 -1 0.1024
-2 -1 0 0.0915
1 2 2 0.1101
-1 1 2 0.1028
-1 0 0 0.0346
1 0 0 0.0322
27 1 -1 0.0400
7 -3 4 0.1126
-26 1 -2 0.0790
23 2 2 0.0628
14 0 4 0.0934
-10 0 -5 0.0964
-21 -2 -3 0.0867
-23 -3 0 0.0653
26 2 1 0.0396
-25 -3 1 0.0547
27 2 0 0.0313
-27 0 1 0.0350
-28 0 0 0.0371
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
N2 N1 C2 114.3(3) . . ?
N3 N2 N1 172.9(6) . . ?
N5 N4 C3 111.1(9) . . ?
N6 N5 N4 176.4(18) . . ?
C7 N7 H7 112.4(15) . . ?
C10 N7 H7 119.4(15) . . ?
C10 N7 C7 128.10(19) . . ?
C2 C1 H1A 109.9 . . ?
C3 C1 H1B 101.1 . . ?
C3 C1 C4 115.5(5) . . ?
C4 C1 H1A 109.9 . . ?
C4 C1 H1B 101.1 . . ?
C4 C1 C2 111.1(2) . . ?
C12 C1 H1A 109.9 . . ?
C12 C1 H1B 101.1 . . ?
C12 C1 C2 104.0(2) . . ?
C12 C1 C3 121.9(5) . . ?
C12 C1 C4 111.74(19) . . ?
N1 C2 C1 109.2(3) . . ?
N1 C2 H2A 109.8 . . ?
N1 C2 H2B 109.8 . . ?
C1 C2 H2A 109.8 . . ?
C1 C2 H2B 109.8 . . ?
H2A C2 H2B 108.3 . . ?
N4 C3 C1 99.2(7) . . ?
N4 C3 H3A 111.9 . . ?
N4 C3 H3B 111.9 . . ?
C1 C3 H3A 111.9 . . ?
C1 C3 H3B 111.9 . . ?
H3A C3 H3B 109.6 . . ?
C5 C4 C1 120.7(2) . . ?
C9 C4 C1 121.4(2) . . ?
C9 C4 C5 117.9(2) . . ?
C4 C5 H5 119.4 . . ?
C6 C5 C4 121.1(2) . . ?
C6 C5 H5 119.4 . . ?
C5 C6 H6 119.7 . . ?
C5 C6 C7 120.5(2) . . ?
C7 C6 H6 119.7 . . ?
C6 C7 N7 117.16(19) . . ?
C6 C7 C8 118.9(2) . . ?
C8 C7 N7 123.92(19) . . ?
C7 C8 H8 120.3 . . ?
C9 C8 C7 119.3(2) . . ?
C9 C8 H8 120.3 . . ?
C4 C9 C8 122.2(2) . . ?
C4 C9 H9 118.9 . . ?
C8 C9 H9 118.9 . . ?
O1 C10 N7 123.0(2) . . ?
O1 C10 C11 121.41(19) . . ?
N7 C10 C11 115.57(19) . . ?
C10 C11 H11A 109.5 . . ?
C10 C11 H11B 109.5 . . ?
C10 C11 H11C 109.5 . . ?
H11A C11 H11B 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C13 C12 C1 175.2(3) . . ?
C12 C13 C14 177.3(3) . . ?
C15 C14 C13 121.7(2) . . ?
C15 C14 C19 118.9(2) . . ?
C19 C14 C13 119.4(2) . . ?
C14 C15 H15 120.1 . . ?
C14 C15 C16 119.8(2) . . ?
C16 C15 H15 120.1 . . ?
C15 C16 H16 119.7 . . ?
C17 C16 C15 120.5(3) . . ?
C17 C16 H16 119.7 . . ?
C16 C17 H17 120.0 . . ?
C16 C17 C18 119.9(3) . . ?
C18 C17 H17 120.0 . . ?
C17 C18 H18 120.0 . . ?
C19 C18 C17 120.0(3) . . ?
C19 C18 H18 120.0 . . ?
C14 C19 H19 119.6 . . ?
C18 C19 C14 120.8(2) . . ?
C18 C19 H19 119.6 . . ?
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 C10 1.233(2) . ?
N1 N2 1.221(4) . ?
N1 C2 1.488(4) . ?
N2 N3 1.142(8) . ?
N4 N5 1.188(11) . ?
N4 C3 1.488(12) . ?
N5 N6 1.157(14) . ?
N7 H7 0.84(3) . ?
N7 C7 1.412(3) . ?
N7 C10 1.350(3) . ?
C1 H1A 1.0000 . ?
C1 H1B 1.0000 . ?
C1 C2 1.566(4) . ?
C1 C3 1.517(8) . ?
C1 C4 1.522(3) . ?
C1 C12 1.468(3) . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C4 C5 1.390(3) . ?
C4 C9 1.381(3) . ?
C5 H5 0.9500 . ?
C5 C6 1.380(3) . ?
C6 H6 0.9500 . ?
C6 C7 1.391(3) . ?
C7 C8 1.398(3) . ?
C8 H8 0.9500 . ?
C8 C9 1.385(3) . ?
C9 H9 0.9500 . ?
C10 C11 1.497(3) . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 0.9800 . ?
C12 C13 1.195(3) . ?
C13 C14 1.439(3) . ?
C14 C15 1.390(3) . ?
C14 C19 1.395(3) . ?
C15 H15 0.9500 . ?
C15 C16 1.393(3) . ?
C16 H16 0.9500 . ?
C16 C17 1.374(4) . ?
C17 H17 0.9500 . ?
C17 C18 1.385(4) . ?
C18 H18 0.9500 . ?
C18 C19 1.375(4) . ?
C19 H19 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
N7 H7 O1 0.84(3) 2.08(3) 2.918(2) 175(2) 3_655 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
N2 N1 C2 C1 144.8(3) . . . . ?
N5 N4 C3 C1 -140.7(9) . . . . ?
N7 C7 C8 C9 -178.95(19) . . . . ?
C1 C4 C5 C6 -179.0(2) . . . . ?
C1 C4 C9 C8 179.4(2) . . . . ?
C2 C1 C4 C5 -73.6(3) . . . . ?
C2 C1 C4 C9 106.3(3) . . . . ?
C3 C1 C4 C5 -103.0(5) . . . . ?
C3 C1 C4 C9 76.9(6) . . . . ?
C4 C1 C2 N1 -62.0(4) . . . . ?
C4 C1 C3 N4 68.8(9) . . . . ?
C4 C5 C6 C7 0.0(3) . . . . ?
C5 C4 C9 C8 -0.7(3) . . . . ?
C5 C6 C7 N7 179.31(19) . . . . ?
C5 C6 C7 C8 -1.6(3) . . . . ?
C6 C7 C8 C9 2.0(3) . . . . ?
C7 N7 C10 O1 -2.2(3) . . . . ?
C7 N7 C10 C11 178.25(19) . . . . ?
C7 C8 C9 C4 -0.9(3) . . . . ?
C9 C4 C5 C6 1.1(3) . . . . ?
C10 N7 C7 C6 -162.5(2) . . . . ?
C10 N7 C7 C8 18.5(3) . . . . ?
C12 C1 C2 N1 177.6(3) . . . . ?
C12 C1 C3 N4 -72.4(9) . . . . ?
C12 C1 C4 C5 42.1(3) . . . . ?
C12 C1 C4 C9 -138.0(2) . . . . ?
C13 C14 C15 C16 179.5(2) . . . . ?
C13 C14 C19 C18 -178.7(2) . . . . ?
C14 C15 C16 C17 -0.5(4) . . . . ?
C15 C14 C19 C18 0.8(4) . . . . ?
C15 C16 C17 C18 0.2(4) . . . . ?
C16 C17 C18 C19 0.6(4) . . . . ?
C17 C18 C19 C14 -1.1(4) . . . . ?
C19 C14 C15 C16 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
1.0005 -0.9998 0.0005 -0.1462 0.0421 -0.0662
2.0013 -0.0008 -0.9999 -0.1076 -0.0212 0.1868
-2.0013 0.0008 0.9999 0.1076 0.0212 -0.1868
0.9986 1.9998 -0.0005 0.2760 0.0118 0.1737
1.0027 -2.0007 -0.9994 -0.3836 -0.0330 0.0131
-1.0027 2.0007 0.9994 0.3836 0.0330 -0.0131
0.9992 1.0000 -0.0002 0.1353 0.0219 0.0937
1.0021 -1.0008 -0.9997 -0.2429 -0.0431 0.0931
-1.9991 -1.0001 0.0001 -0.1298 -0.0538 -0.1075
0.9953 2.0020 1.9998 0.4693 0.1821 -0.1448
-1.0037 1.0019 1.9998 0.3395 0.1282 -0.2523
-0.9999 -0.0001 -0.0001 0.0055 -0.0320 -0.0138
0.9999 0.0001 0.0001 -0.0055 0.0320 0.0138
27.0332 0.9375 -1.2824 -0.1409 0.7454 0.6516
7.2107 -3.2213 3.9742 -0.1100 0.6014 -0.7913
-26.0243 1.3865 -1.6116 0.1834 -0.9830 0.0091
22.8210 2.4110 2.1864 0.4244 0.8914 0.1588
13.9828 0.3490 4.2413 0.3811 0.8047 -0.4552
-9.9752 0.3492 -4.5637 -0.3360 -0.7111 0.6176
-20.9494 -1.8454 -2.9531 -0.4291 -0.9026 0.0344
-23.2357 -3.4917 0.4403 -0.3209 -0.6701 -0.6693
26.4206 2.1139 0.6065 0.2103 0.8749 0.4363
-25.3193 -2.6685 0.6176 -0.1764 -0.7298 -0.6605
26.9270 1.9341 -0.1437 0.1098 0.8290 0.5484
-27.4176 -0.3097 1.2325 0.2266 -0.7682 -0.5988
-28.2069 0.4590 0.3936 0.2583 -0.8726 -0.4145
