#------------------------------------------------------------------------------
#$Date: 2022-03-02 03:51:53 +0200 (Wed, 02 Mar 2022) $
#$Revision: 273201 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/24/45/7244535.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_7244535
loop_
_publ_author_name
'Zhou, Yang'
'Maisonneuve, Stéphane'
'Casimiro, Lorenzo'
'Retailleau, Pascal'
'Xie, Juan'
'Maurel, François'
'Métivier, Rémi'
_publ_section_title
;
 Photoisomerization of a
 4-dicyanomethylene-2-methyl-6-(p-dimethylaminostyryl)-4H-pyran analog
 dye: a combined photophysical and theoretical investigation
;
_journal_name_full               'Physical Chemistry Chemical Physics'
_journal_paper_doi               10.1039/D1CP05170A
_journal_year                    2022
_chemical_formula_moiety         'C23 H24 N6 O'
_chemical_formula_sum            'C23 H24 N6 O'
_chemical_formula_weight         400.48
_chemical_name_systematic
(E)-2-(2-(4-((2-azidoethyl)(methyl)amino)styryl)-6-(tert-butyl)-4H-pyran-4-ylidene)malononitrile
_space_group_crystal_system      orthorhombic
_space_group_IT_number           62
_space_group_name_Hall           '-P 2ac 2n'
_space_group_name_H-M_alt        'P n m a'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     other
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2018/3
_audit_update_record
;
2021-11-10 deposited with the CCDC.	2022-02-09 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   29.8656(17)
_cell_length_b                   7.1127(4)
_cell_length_c                   10.0461(5)
_cell_measurement_reflns_used    4858
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      29.0830
_cell_measurement_theta_min      3.1740
_cell_volume                     2134.0(2)
_computing_cell_refinement       'CrysAlisPro 1.171.41.96a (Rigaku OD, 2021)'
_computing_data_collection       'CrysAlisPro 1.171.41.96a (Rigaku OD, 2021)'
_computing_data_reduction        'CrysAlisPro 1.171.41.96a (Rigaku OD, 2021)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_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 0.997
_diffrn_measured_fraction_theta_max 0.997
_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  0.0186
_diffrn_reflns_av_unetI/netI     0.0167
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       36
_diffrn_reflns_limit_h_min       -31
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            13711
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.019
_diffrn_reflns_theta_min         2.881
_diffrn_source                   'microfocus sealed X-ray tube'
_diffrn_source_type              'Rigaku micromax 003'
_exptl_absorpt_coefficient_mu    0.080
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.68649
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.41.118a (Rigaku Oxford Diffraction, 2021)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            red
_exptl_crystal_density_diffrn    1.245
_exptl_crystal_description       tab
_exptl_crystal_F_000             848
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.13
_refine_diff_density_max         0.724
_refine_diff_density_min         -0.510
_refine_diff_density_rms         0.088
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.091
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     188
_refine_ls_number_reflns         2280
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.091
_refine_ls_R_factor_all          0.0731
_refine_ls_R_factor_gt           0.0659
_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)+(0.1286P)²+0.5387P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2012
_refine_ls_wR_factor_ref         0.2093
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1921
_reflns_number_total             2283
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d1cp05170a2.cif
_cod_data_source_block           pnma
_cod_database_code               7244535
_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+1/2, -y+1/2, -z+1/2'
'-x, y+1/2, -z'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'-x-1/2, y-1/2, z-1/2'
'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
C1 C 0.32833(8) 0.250000 0.3873(2) 0.0438(6) Uani 1 2 d S T P . .
H1 H 0.358207 0.250000 0.413391 0.053 Uiso 1 2 calc R U P . .
N1 N 0.24012(9) 0.250000 0.7935(3) 0.0862(10) Uani 1 2 d S T P . .
N2 N 0.38263(8) 0.250000 0.7181(3) 0.0831(9) Uani 1 2 d S T P . .
C2 C 0.31819(7) 0.250000 0.2575(2) 0.0422(6) Uani 1 2 d S T P . .
N3 N 0.00919(7) 0.250000 -0.0881(2) 0.0674(8) Uani 1 2 d S T P . .
O3 O 0.27463(5) 0.250000 0.21476(15) 0.0471(5) Uani 1 2 d S T P . .
C4 C 0.24075(7) 0.250000 0.3059(2) 0.0449(6) Uani 1 2 d S T P . .
C6 C 0.29391(7) 0.250000 0.4869(2) 0.0413(5) Uani 1 2 d S T P . .
C5 C 0.24955(7) 0.250000 0.4374(2) 0.0450(6) Uani 1 2 d S T P . .
H5 H 0.225810 0.250000 0.497292 0.054 Uiso 1 2 calc R U P . .
C7 C 0.30321(8) 0.250000 0.6218(2) 0.0453(6) Uani 1 2 d S T P . .
C9 C 0.19651(8) 0.250000 0.2503(3) 0.0490(6) Uani 1 2 d S T P . .
H9 H 0.172830 0.250000 0.310414 0.059 Uiso 1 2 calc R U P . .
C8 C 0.34993(8) 0.250000 0.1405(2) 0.0477(6) Uani 1 2 d S T P . .
C10 C 0.39840(8) 0.250000 0.1895(3) 0.0644(8) Uani 1 2 d S T P . .
H10A H 0.411425 0.250000 0.112762 0.097 Uiso 1 2 d R U P . .
H10 H 0.406643 0.127275 0.234339 0.097 Uiso 1 1 d R U . . .
C12 C 0.34143(7) 0.0742(3) 0.0567(2) 0.0685(6) Uani 1 1 d . . . . .
H12A H 0.361760 0.072186 -0.017268 0.103 Uiso 1 1 calc R U . . .
H12B H 0.311184 0.075656 0.024421 0.103 Uiso 1 1 calc R U . . .
H12C H 0.346014 -0.035791 0.110464 0.103 Uiso 1 1 calc R U . . .
C24 C 0.34741(9) 0.250000 0.6732(2) 0.0554(7) Uani 1 2 d S T P . .
C23 C 0.26822(8) 0.250000 0.7178(2) 0.0540(7) Uani 1 2 d S T P . .
C14 C 0.14044(8) 0.250000 0.0677(2) 0.0465(6) Uani 1 2 d S T P . .
C13 C 0.18573(8) 0.250000 0.1208(2) 0.0481(6) Uani 1 2 d S T P . .
H13 H 0.209165 0.250000 0.059794 0.058 Uiso 1 2 calc R U P . .
C15 C 0.10252(8) 0.250000 0.1487(3) 0.0565(7) Uani 1 2 d S T P . .
H15 H 0.106257 0.250000 0.240593 0.068 Uiso 1 2 calc R U P . .
C16 C 0.05989(8) 0.250000 0.0977(3) 0.0558(7) Uani 1 2 d S T P . .
H16 H 0.035610 0.250000 0.155673 0.067 Uiso 1 2 calc R U P . .
C17 C 0.05224(8) 0.250000 -0.0394(3) 0.0510(6) Uani 1 2 d S T P . .
C18 C 0.09020(8) 0.250000 -0.1216(3) 0.0553(7) Uani 1 2 d S T P . .
H18 H 0.086552 0.250000 -0.213574 0.066 Uiso 1 2 calc R U P . .
C19 C 0.13282(8) 0.250000 -0.0689(3) 0.0515(6) Uani 1 2 d S T P . .
H19 H 0.157223 0.250000 -0.126365 0.062 Uiso 1 2 calc R U P . .
C20 C -0.02877(8) 0.250000 0.0010(3) 0.0652(8) Uani 1 2 d S T P . .
H20A H -0.053608 0.250000 -0.040802 0.098 Uiso 1 2 d R U P . .
H20B H -0.026413 0.143438 0.068489 0.098 Uiso 1 1 d R U . . .
C21 C -0.00047(13) 0.1820(6) -0.2270(4) 0.0619(11) Uani 0.5 1 d . . P . .
H21A H -0.026799 0.102211 -0.227321 0.074 Uiso 0.5 1 calc R U P . .
H21B H 0.024675 0.110229 -0.260898 0.074 Uiso 0.5 1 calc R U P . .
C22 C -0.0083(2) 0.1448(10) -0.3127(5) 0.0969(19) Uani 0.5 1 d . . P . .
H22A H 0.015098 0.053866 -0.294624 0.116 Uiso 0.5 1 calc R U P . .
H22B H -0.036649 0.088311 -0.287574 0.116 Uiso 0.5 1 calc R U P . .
N4 N -0.0090(2) 0.1833(11) -0.4515(6) 0.139(4) Uani 0.5 1 d . . P . .
N5 N 0.0286(2) 0.250000 -0.4979(5) 0.177(3) Uani 1 2 d S T P . .
N6 N 0.0604(2) 0.250000 -0.5471(6) 0.209(4) Uani 1 2 d S T P . .
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
C2 C1 C6 121.2(2) . . ?
C2 C1 H1 119.4 . . ?
C6 C1 H1 119.4 . . ?
C1 C2 O3 121.3(2) . . ?
C1 C2 C8 128.0(2) . . ?
O3 C2 C8 110.62(19) . . ?
C17 N3 C20 120.9(2) . . ?
C17 N3 C21 120.6(2) . . ?
C20 N3 C21 115.1(2) . . ?
C17 N3 C21 120.6(2) . 8_565 ?
C20 N3 C21 115.1(2) . 8_565 ?
C21 N3 C21 37.5(3) . 8_565 ?
C4 O3 C2 119.59(18) . . ?
C5 C4 O3 120.9(2) . . ?
C5 C4 C9 124.2(2) . . ?
O3 C4 C9 114.9(2) . . ?
C7 C6 C5 122.2(2) . . ?
C7 C6 C1 122.6(2) . . ?
C5 C6 C1 115.2(2) . . ?
C4 C5 C6 121.8(2) . . ?
C4 C5 H5 119.1 . . ?
C6 C5 H5 119.1 . . ?
C6 C7 C24 122.9(2) . . ?
C6 C7 C23 121.1(2) . . ?
C24 C7 C23 116.0(2) . . ?
C13 C9 C4 126.8(2) . . ?
C13 C9 H9 116.6 . . ?
C4 C9 H9 116.6 . . ?
C2 C8 C12 108.92(14) . . ?
C2 C8 C12 108.92(14) . 8_565 ?
C12 C8 C12 109.8(2) . 8_565 ?
C2 C8 C10 110.13(19) . . ?
C12 C8 C10 109.53(14) . . ?
C12 C8 C10 109.53(14) 8_565 . ?
C8 C10 H10A 98.0 . . ?
C8 C10 H10 111.9 . . ?
H10A C10 H10 106.7 . . ?
C8 C10 H10 111.92(5) . 8_565 ?
H10A C10 H10 106.7 . 8_565 ?
H10 C10 H10 119.0 . 8_565 ?
C8 C12 H12A 109.5 . . ?
C8 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
C8 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
N2 C24 C7 178.1(3) . . ?
N1 C23 C7 179.5(3) . . ?
C19 C14 C15 116.3(2) . . ?
C19 C14 C13 120.9(2) . . ?
C15 C14 C13 122.8(2) . . ?
C9 C13 C14 125.4(2) . . ?
C9 C13 H13 117.3 . . ?
C14 C13 H13 117.3 . . ?
C16 C15 C14 122.4(2) . . ?
C16 C15 H15 118.8 . . ?
C14 C15 H15 118.8 . . ?
C15 C16 C17 121.3(2) . . ?
C15 C16 H16 119.3 . . ?
C17 C16 H16 119.3 . . ?
N3 C17 C16 120.2(2) . . ?
N3 C17 C18 123.1(2) . . ?
C16 C17 C18 116.7(2) . . ?
C19 C18 C17 121.3(2) . . ?
C19 C18 H18 119.3 . . ?
C17 C18 H18 119.3 . . ?
C18 C19 C14 122.0(2) . . ?
C18 C19 H19 119.0 . . ?
C14 C19 H19 119.0 . . ?
N3 C20 H20A 112.2 . . ?
N3 C20 H20B 111.0 . . ?
H20A C20 H20B 112.8 . . ?
N3 C20 H20B 110.97(9) . 8_565 ?
H20A C20 H20B 112.8 . 8_565 ?
H20B C20 H20B 96.0 . 8_565 ?
N3 C21 C22 107.1(3) . 8_565 ?
N3 C21 H21A 110.3 . . ?
C22 C21 H21A 110.3 8_565 . ?
N3 C21 H21B 110.3 . . ?
C22 C21 H21B 110.3 8_565 . ?
H21A C21 H21B 108.5 . . ?
N4 C22 C21 113.7(5) . 8_565 ?
N4 C22 H22A 108.8 . . ?
C21 C22 H22A 108.8 8_565 . ?
N4 C22 H22B 108.8 . . ?
C21 C22 H22B 108.8 8_565 . ?
H22A C22 H22B 107.7 . . ?
N4 N4 N5 68.7(3) 8_565 . ?
N4 N4 C22 101.1(4) 8_565 . ?
N5 N4 C22 114.1(5) . . ?
N4 N4 C22 48.8(3) 8_565 8_565 ?
N5 N4 C22 91.1(5) . 8_565 ?
C22 N4 C22 52.3(5) . 8_565 ?
N6 N5 N4 158.1(4) . . ?
N6 N5 N4 158.1(4) . 8_565 ?
N4 N5 N4 42.6(7) . 8_565 ?
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
C1 C2 1.339(3) . ?
C1 C6 1.434(3) . ?
C1 H1 0.9300 . ?
N1 C23 1.133(3) . ?
N2 C24 1.145(3) . ?
C2 O3 1.370(3) . ?
C2 C8 1.510(3) . ?
N3 C17 1.376(3) . ?
N3 C20 1.444(3) . ?
N3 C21 1.505(5) . ?
N3 C21 1.505(5) 8_565 ?
O3 C4 1.365(3) . ?
C4 C5 1.347(4) . ?
C4 C9 1.435(3) . ?
C6 C7 1.383(3) . ?
C6 C5 1.415(3) . ?
C5 H5 0.9300 . ?
C7 C24 1.417(3) . ?
C7 C23 1.422(3) . ?
C9 C13 1.341(4) . ?
C9 H9 0.9300 . ?
C8 C12 1.529(2) . ?
C8 C12 1.529(2) 8_565 ?
C8 C10 1.529(4) . ?
C10 H10A 0.8630 . ?
C10 H10 1.0129 . ?
C10 H10 1.0129 8_565 ?
C12 H12A 0.9600 . ?
C12 H12B 0.9600 . ?
C12 H12C 0.9600 . ?
C14 C19 1.391(3) . ?
C14 C15 1.395(3) . ?
C14 C13 1.454(3) . ?
C13 H13 0.9300 . ?
C15 C16 1.372(3) . ?
C15 H15 0.9300 . ?
C16 C17 1.396(4) . ?
C16 H16 0.9300 . ?
C17 C18 1.403(3) . ?
C18 C19 1.379(3) . ?
C18 H18 0.9300 . ?
C19 H19 0.9300 . ?
C20 H20A 0.8521 . ?
C20 H20B 1.0197 . ?
C20 H20B 1.0197 8_565 ?
C21 C22 1.521(7) 8_565 ?
C21 H21A 0.9700 . ?
C21 H21B 0.9700 . ?
C22 N4 1.421(8) . ?
C22 H22A 0.9700 . ?
C22 H22B 0.9700 . ?
N4 N4 0.949(16) 8_565 ?
N4 N5 1.306(8) . ?
N5 N6 1.069(7) . ?
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
C6 C1 C2 O3 0.000(0) . . . . ?
C6 C1 C2 C8 180.000(0) . . . . ?
C1 C2 O3 C4 0.000(0) . . . . ?
C8 C2 O3 C4 180.000(0) . . . . ?
C2 O3 C4 C5 0.000(0) . . . . ?
C2 O3 C4 C9 180.000(0) . . . . ?
C2 C1 C6 C7 180.000(0) . . . . ?
C2 C1 C6 C5 0.000(0) . . . . ?
O3 C4 C5 C6 0.000(0) . . . . ?
C9 C4 C5 C6 180.000(0) . . . . ?
C7 C6 C5 C4 180.000(0) . . . . ?
C1 C6 C5 C4 0.000(0) . . . . ?
C5 C6 C7 C24 180.000(0) . . . . ?
C1 C6 C7 C24 0.000(0) . . . . ?
C5 C6 C7 C23 0.000(0) . . . . ?
C1 C6 C7 C23 180.000(0) . . . . ?
C5 C4 C9 C13 180.000(0) . . . . ?
O3 C4 C9 C13 0.000(0) . . . . ?
C1 C2 C8 C12 120.13(15) . . . . ?
O3 C2 C8 C12 -59.87(15) . . . . ?
C1 C2 C8 C12 -120.13(15) . . . 8_565 ?
O3 C2 C8 C12 59.87(15) . . . 8_565 ?
C1 C2 C8 C10 0.000(0) . . . . ?
O3 C2 C8 C10 180.0 . . . . ?
C4 C9 C13 C14 180.000(0) . . . . ?
C19 C14 C13 C9 180.000(0) . . . . ?
C15 C14 C13 C9 0.000(0) . . . . ?
C19 C14 C15 C16 0.0 . . . . ?
C13 C14 C15 C16 180.0 . . . . ?
C14 C15 C16 C17 0.000(0) . . . . ?
C20 N3 C17 C16 0.0 . . . . ?
C21 N3 C17 C16 -158.1(2) . . . . ?
C21 N3 C17 C16 158.1(2) 8_565 . . . ?
C20 N3 C17 C18 180.0 . . . . ?
C21 N3 C17 C18 21.9(2) . . . . ?
C21 N3 C17 C18 -21.9(2) 8_565 . . . ?
C15 C16 C17 N3 180.0 . . . . ?
C15 C16 C17 C18 0.0 . . . . ?
N3 C17 C18 C19 180.0 . . . . ?
C16 C17 C18 C19 0.000(0) . . . . ?
C17 C18 C19 C14 0.0 . . . . ?
C15 C14 C19 C18 0.0 . . . . ?
C13 C14 C19 C18 180.0 . . . . ?
C17 N3 C21 C22 -103.8(3) . . . 8_565 ?
C20 N3 C21 C22 96.9(3) . . . 8_565 ?
C21 N3 C21 C22 -2.2(4) 8_565 . . 8_565 ?
C21 C22 N4 N4 -9.2(5) 8_565 . . 8_565 ?
C21 C22 N4 N5 62.3(8) 8_565 . . . ?
C21 C22 N4 C22 -9.2(5) 8_565 . . 8_565 ?
N4 N4 N5 N6 -166.4(19) 8_565 . . . ?
C22 N4 N5 N6 100.6(18) . . . . ?
C22 N4 N5 N6 149.2(18) 8_565 . . . ?
C22 N4 N5 N4 -93.0(6) . . . 8_565 ?
C22 N4 N5 N4 -44.3(3) 8_565 . . 8_565 ?
