#------------------------------------------------------------------------------
#$Date: 2021-10-06 16:41:48 +0300 (Wed, 06 Oct 2021) $
#$Revision: 269603 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/12/87/7128751.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_7128751
loop_
_publ_author_name
'Goual, Nawel'
'Casimiro, Lorenzo'
'Delattre, Vincent'
'Retailleau, Pascal'
'Maisonneuve, Stéphane'
'Bogliotti, Nicolas'
'Métivier, Rémi'
'Xie, Juan'
'Marinetti, Angela'
'Voituriez, Arnaud'
_publ_section_title
;
 Triazonine-based bistable photoswitches: synthesis, characterization and
 photochromic properties.
;
_journal_issue                   78
_journal_name_full
'Chemical communications (Cambridge, England)'
_journal_page_first              10079
_journal_page_last               10082
_journal_paper_doi               10.1039/d1cc02746h
_journal_volume                  57
_journal_year                    2021
_chemical_formula_moiety         'C17 H17 N3 O2'
_chemical_formula_sum            'C17 H17 N3 O2'
_chemical_formula_weight         295.33
_chemical_name_systematic
;
'ethyl (E)-11,13-dihydro-12H-dibenzo[c,h][1,2,6]triazonine-12-carboxylate'
;
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     other
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2018/3
_audit_update_record
;
2021-03-05 deposited with the CCDC.	2021-08-02 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   5.0393(3)
_cell_length_b                   11.5613(6)
_cell_length_c                   26.3881(15)
_cell_measurement_reflns_used    4102
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      25.4810
_cell_measurement_theta_min      3.6750
_cell_volume                     1537.39(15)
_computing_cell_refinement       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2015b)'
_computing_structure_solution    'SHELXT (Sheldrick, 2015a)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'Dectris PILATUS3 R 200K-A area detector'
_diffrn_detector_area_resol_mean 5.811
_diffrn_detector_type            'Hybrid Photon Counting area detector'
_diffrn_measured_fraction_theta_full 0.991
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measurement_device       'kappa gonio four-circle diffractometer'
_diffrn_measurement_device_type  'Rigaku XtaLAB PRO'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_collimation
'Rigaku Integrated Confocal MaxFlux double bounce multi-layer mirror optics'
_diffrn_radiation_monochromator  none
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0379
_diffrn_reflns_av_unetI/netI     0.0439
_diffrn_reflns_Laue_measured_fraction_full 0.991
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       32
_diffrn_reflns_limit_l_min       -31
_diffrn_reflns_number            9387
_diffrn_reflns_point_group_measured_fraction_full 0.982
_diffrn_reflns_point_group_measured_fraction_max 0.972
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.369
_diffrn_reflns_theta_min         3.524
_diffrn_source                   'microfocus sealed X-ray tube'
_diffrn_source_type              'Rigaku micromax 003'
_exptl_absorpt_coefficient_mu    0.086
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.43897
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.46 (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            brown
_exptl_crystal_density_diffrn    1.276
_exptl_crystal_description       stick
_exptl_crystal_F_000             624
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.07
_exptl_crystal_size_min          0.04
_refine_diff_density_max         0.186
_refine_diff_density_min         -0.213
_refine_diff_density_rms         0.064
_refine_ls_abs_structure_details
;
Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   0.4(17)
_refine_ls_extinction_coef       0.025(5)
_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   1.058
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     202
_refine_ls_number_reflns         3063
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.058
_refine_ls_R_factor_all          0.0498
_refine_ls_R_factor_gt           0.0384
_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)+(0.0606P)²+0.0035P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0931
_refine_ls_wR_factor_ref         0.0985
_reflns_Friedel_coverage         0.653
_reflns_Friedel_fraction_full    0.968
_reflns_Friedel_fraction_max     0.944
_reflns_number_gt                2567
_reflns_number_total             3072
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d1cc02746h2.cif
_cod_data_source_block           compound_E-2c
_cod_depositor_comments
'Adding full bibliography for 7128749--7128753.cif.'
_cod_original_cell_volume        1537.41(16)
_cod_database_code               7128751
_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.
;
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -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 0.4802(4) 0.55052(14) 0.45809(5) 0.0675(5) Uani 1 1 d . . . . .
C1 C 0.5269(4) 0.26939(16) 0.37894(7) 0.0463(5) Uani 1 1 d . . . . .
N1 N 0.3689(4) 0.32032(13) 0.33992(6) 0.0487(4) Uani 1 1 d . . . . .
O2 O 0.3263(3) 0.67523(11) 0.39924(5) 0.0568(4) Uani 1 1 d . . . . .
C2 C 0.7302(4) 0.33187(18) 0.40294(7) 0.0477(5) Uani 1 1 d . . . . .
N2 N 0.5084(4) 0.38277(13) 0.31221(6) 0.0456(4) Uani 1 1 d . . . . .
N3 N 0.6296(4) 0.54398(13) 0.37705(6) 0.0451(4) Uani 1 1 d . . . . .
C3 C 0.8242(5) 0.45380(18) 0.39053(8) 0.0532(5) Uani 1 1 d . . . . .
H3A H 0.923241 0.481685 0.419587 0.064 Uiso 1 1 calc R U . . .
H3AB H 0.948740 0.447766 0.362632 0.064 Uiso 1 1 calc R U . . .
C4 C 0.6491(5) 0.60324(17) 0.32773(7) 0.0505(5) Uani 1 1 d . . . . .
H4A H 0.820129 0.584675 0.312963 0.061 Uiso 1 1 calc R U . . .
H4AB H 0.646357 0.685969 0.333831 0.061 Uiso 1 1 calc R U . . .
C5 C 0.4365(4) 0.57548(15) 0.28903(7) 0.0444(5) Uani 1 1 d . . . . .
C6 C 0.3644(5) 0.46068(16) 0.28042(7) 0.0448(5) Uani 1 1 d . . . . .
C7 C 0.4803(5) 0.58616(16) 0.41507(7) 0.0469(5) Uani 1 1 d . . . . .
C11 C 0.6025(6) 0.1056(2) 0.43240(9) 0.0696(7) Uani 1 1 d . . . . .
H11 H 0.560121 0.030538 0.442195 0.083 Uiso 1 1 calc R U . . .
C10 C 0.4599(6) 0.15971(18) 0.39497(9) 0.0598(6) Uani 1 1 d . . . . .
H10 H 0.316424 0.121939 0.380239 0.072 Uiso 1 1 calc R U . . .
C9 C 0.0447(9) 0.8342(3) 0.41643(12) 0.1019(12) Uani 1 1 d . . . . .
H9A H -0.043499 0.876557 0.442796 0.153 Uiso 1 1 calc R U . . .
H9B H -0.083323 0.809031 0.391843 0.153 Uiso 1 1 calc R U . . .
H9C H 0.173449 0.883098 0.400315 0.153 Uiso 1 1 calc R U . . .
C8 C 0.1770(7) 0.7341(2) 0.43812(10) 0.0729(8) Uani 1 1 d . . . . .
H8A H 0.295372 0.758612 0.465045 0.088 Uiso 1 1 calc R U . . .
H8AB H 0.046445 0.681893 0.452478 0.088 Uiso 1 1 calc R U . . .
C15 C 0.0635(6) 0.5171(2) 0.21521(9) 0.0649(7) Uani 1 1 d . . . . .
H15 H -0.059336 0.498117 0.190246 0.078 Uiso 1 1 calc R U . . .
C12 C 0.8076(6) 0.1631(2) 0.45516(9) 0.0702(7) Uani 1 1 d . . . . .
H12 H 0.907461 0.126562 0.480102 0.084 Uiso 1 1 calc R U . . .
C16 C 0.1320(6) 0.63085(19) 0.22314(8) 0.0611(6) Uani 1 1 d . . . . .
H16 H 0.055648 0.688534 0.203375 0.073 Uiso 1 1 calc R U . . .
C13 C 0.8665(5) 0.2748(2) 0.44123(8) 0.0628(6) Uani 1 1 d . . . . .
H13 H 1.002334 0.313491 0.458032 0.075 Uiso 1 1 calc R U . . .
C17 C 0.3134(5) 0.66002(17) 0.26024(8) 0.0549(6) Uani 1 1 d . . . . .
H17 H 0.353357 0.737455 0.265958 0.066 Uiso 1 1 calc R U . . .
C14 C 0.1777(5) 0.43063(18) 0.24447(7) 0.0562(6) Uani 1 1 d . . . . .
H14 H 0.129238 0.353701 0.239926 0.067 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 0.0033 0.0016 '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 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
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
C10 C1 C2 120.88(19) . . ?
C10 C1 N1 117.6(2) . . ?
C2 C1 N1 121.30(18) . . ?
N2 N1 C1 110.35(17) . . ?
C7 O2 C8 115.96(16) . . ?
C13 C2 C1 116.4(2) . . ?
C13 C2 C3 116.2(2) . . ?
C1 C2 C3 127.32(19) . . ?
N1 N2 C6 115.06(18) . . ?
C7 N3 C4 121.80(16) . . ?
C7 N3 C3 116.62(16) . . ?
C4 N3 C3 119.83(17) . . ?
N3 C3 C2 119.97(18) . . ?
N3 C3 H3A 107.3 . . ?
C2 C3 H3A 107.3 . . ?
N3 C3 H3AB 107.3 . . ?
C2 C3 H3AB 107.3 . . ?
H3A C3 H3AB 106.9 . . ?
N3 C4 C5 116.73(16) . . ?
N3 C4 H4A 108.1 . . ?
C5 C4 H4A 108.1 . . ?
N3 C4 H4AB 108.1 . . ?
C5 C4 H4AB 108.1 . . ?
H4A C4 H4AB 107.3 . . ?
C17 C5 C6 117.75(19) . . ?
C17 C5 C4 122.50(18) . . ?
C6 C5 C4 119.72(18) . . ?
C14 C6 C5 121.94(19) . . ?
C14 C6 N2 126.22(18) . . ?
C5 C6 N2 111.84(18) . . ?
O1 C7 N3 125.3(2) . . ?
O1 C7 O2 123.29(19) . . ?
N3 C7 O2 111.45(16) . . ?
C12 C11 C10 119.3(2) . . ?
C12 C11 H11 120.3 . . ?
C10 C11 H11 120.3 . . ?
C11 C10 C1 120.8(2) . . ?
C11 C10 H10 119.6 . . ?
C1 C10 H10 119.6 . . ?
C8 C9 H9A 109.5 . . ?
C8 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
C8 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
O2 C8 C9 109.6(2) . . ?
O2 C8 H8A 109.8 . . ?
C9 C8 H8A 109.8 . . ?
O2 C8 H8AB 109.8 . . ?
C9 C8 H8AB 109.8 . . ?
H8A C8 H8AB 108.2 . . ?
C16 C15 C14 120.0(2) . . ?
C16 C15 H15 120.0 . . ?
C14 C15 H15 120.0 . . ?
C11 C12 C13 120.2(2) . . ?
C11 C12 H12 119.9 . . ?
C13 C12 H12 119.9 . . ?
C15 C16 C17 120.5(2) . . ?
C15 C16 H16 119.8 . . ?
C17 C16 H16 119.8 . . ?
C12 C13 C2 122.3(3) . . ?
C12 C13 H13 118.9 . . ?
C2 C13 H13 118.9 . . ?
C16 C17 C5 120.87(19) . . ?
C16 C17 H17 119.6 . . ?
C5 C17 H17 119.6 . . ?
C6 C14 C15 118.9(2) . . ?
C6 C14 H14 120.5 . . ?
C15 C14 H14 120.5 . . ?
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 C7 1.207(2) . ?
C1 C10 1.379(3) . ?
C1 C2 1.404(3) . ?
C1 N1 1.429(3) . ?
N1 N2 1.245(2) . ?
O2 C7 1.355(3) . ?
O2 C8 1.443(3) . ?
C2 C13 1.389(3) . ?
C2 C3 1.523(3) . ?
N2 C6 1.429(3) . ?
N3 C7 1.346(3) . ?
N3 C4 1.474(2) . ?
N3 C3 1.475(3) . ?
C3 H3A 0.9700 . ?
C3 H3AB 0.9700 . ?
C4 C5 1.514(3) . ?
C4 H4A 0.9700 . ?
C4 H4AB 0.9700 . ?
C5 C17 1.385(3) . ?
C5 C6 1.395(3) . ?
C6 C14 1.381(3) . ?
C11 C12 1.368(4) . ?
C11 C10 1.372(3) . ?
C11 H11 0.9300 . ?
C10 H10 0.9300 . ?
C9 C8 1.453(4) . ?
C9 H9A 0.9600 . ?
C9 H9B 0.9600 . ?
C9 H9C 0.9600 . ?
C8 H8A 0.9700 . ?
C8 H8AB 0.9700 . ?
C15 C16 1.376(4) . ?
C15 C14 1.388(3) . ?
C15 H15 0.9300 . ?
C12 C13 1.376(4) . ?
C12 H12 0.9300 . ?
C16 C17 1.381(3) . ?
C16 H16 0.9300 . ?
C13 H13 0.9300 . ?
C17 H17 0.9300 . ?
C14 H14 0.9300 . ?
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
C3 H3AB N1 0.97 2.65 3.421(3) 136.8 1_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
C10 C1 N1 N2 -146.22(19) . . . . ?
C2 C1 N1 N2 38.6(2) . . . . ?
C10 C1 C2 C13 3.4(3) . . . . ?
N1 C1 C2 C13 178.39(19) . . . . ?
C10 C1 C2 C3 -178.8(2) . . . . ?
N1 C1 C2 C3 -3.8(3) . . . . ?
C1 N1 N2 C6 -164.57(15) . . . . ?
C7 N3 C3 C2 73.3(2) . . . . ?
C4 N3 C3 C2 -121.5(2) . . . . ?
C13 C2 C3 N3 -142.9(2) . . . . ?
C1 C2 C3 N3 39.3(3) . . . . ?
C7 N3 C4 C5 -86.0(2) . . . . ?
C3 N3 C4 C5 109.6(2) . . . . ?
N3 C4 C5 C17 135.9(2) . . . . ?
N3 C4 C5 C6 -46.0(3) . . . . ?
C17 C5 C6 C14 0.2(3) . . . . ?
C4 C5 C6 C14 -177.96(19) . . . . ?
C17 C5 C6 N2 179.33(18) . . . . ?
C4 C5 C6 N2 1.2(3) . . . . ?
N1 N2 C6 C14 -58.9(3) . . . . ?
N1 N2 C6 C5 122.01(18) . . . . ?
C4 N3 C7 O1 -170.4(2) . . . . ?
C3 N3 C7 O1 -5.5(3) . . . . ?
C4 N3 C7 O2 9.6(3) . . . . ?
C3 N3 C7 O2 174.50(17) . . . . ?
C8 O2 C7 O1 5.7(3) . . . . ?
C8 O2 C7 N3 -174.3(2) . . . . ?
C12 C11 C10 C1 2.3(4) . . . . ?
C2 C1 C10 C11 -4.6(3) . . . . ?
N1 C1 C10 C11 -179.8(2) . . . . ?
C7 O2 C8 C9 174.1(3) . . . . ?
C10 C11 C12 C13 1.2(4) . . . . ?
C14 C15 C16 C17 -0.3(4) . . . . ?
C11 C12 C13 C2 -2.4(4) . . . . ?
C1 C2 C13 C12 0.1(3) . . . . ?
C3 C2 C13 C12 -177.9(2) . . . . ?
C15 C16 C17 C5 2.2(4) . . . . ?
C6 C5 C17 C16 -2.1(3) . . . . ?
C4 C5 C17 C16 176.0(2) . . . . ?
C5 C6 C14 C15 1.6(3) . . . . ?
N2 C6 C14 C15 -177.4(2) . . . . ?
C16 C15 C14 C6 -1.6(4) . . . . ?
