#------------------------------------------------------------------------------
#$Date: 2024-02-04 12:00:35 +0100 (Sun 04 de Feb de 2024) $
#$Revision: 289320 $
#$URL: svn://www.crystallography.net/cod/cif/7/13/25/7132588.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_7132588
loop_
_publ_author_name
'Zheng, Peng Xuan'
'Ou, Song Lin'
'Qu, Lei Yu'
'Zhang, Ying'
'Jiang, Shi Qing'
'Li, Xiang'
'Wan, Jun Xiong'
'Zhang, Min'
'Bao, Xin'
_publ_section_title
;
 Enriched switching in a donor-acceptor Stenhouse adduct via
 reversible covalent bonding.
;
_journal_issue                   10
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              1333
_journal_page_last               1336
_journal_paper_doi               10.1039/d3cc03160h
_journal_volume                  60
_journal_year                    2024
_chemical_formula_moiety         'C14 H19 N O6'
_chemical_formula_sum            'C14 H19 N O6'
_chemical_formula_weight         297.30
_space_group_crystal_system      orthorhombic
_space_group_IT_number           29
_space_group_name_Hall           'P 2c -2ac'
_space_group_name_H-M_alt        'P c a 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2022-07-18
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2022-09-01 deposited with the CCDC.	2023-12-21 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   17.469(5)
_cell_length_b                   7.599(2)
_cell_length_c                   11.007(3)
_cell_measurement_reflns_used    6292
_cell_measurement_temperature    298
_cell_measurement_theta_max      27.49
_cell_measurement_theta_min      2.33
_cell_volume                     1461.1(7)
_computing_cell_refinement       'SAINT v8.37A (Bruker, 2015)'
_computing_data_reduction        'SAINT v8.37A (Bruker, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      298
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0378
_diffrn_reflns_av_unetI/netI     0.0402
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            13781
_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         27.517
_diffrn_reflns_theta_min         2.332
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.106
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6893
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1294 before and 0.0521 after correction. The Ratio of minimum to maximum transmission is 0.9245. The λ/2 correction factor is Not present.'
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.351
_exptl_crystal_description       rod
_exptl_crystal_F_000             632
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.122
_refine_diff_density_min         -0.114
_refine_diff_density_rms         0.030
_refine_ls_abs_structure_details
;
 Refined as a perfect inversion twin.
;
_refine_ls_abs_structure_Flack   0.5
_refine_ls_extinction_coef       0.019(4)
_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   1.028
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     194
_refine_ls_number_reflns         3349
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.028
_refine_ls_R_factor_all          0.0573
_refine_ls_R_factor_gt           0.0368
_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)+(0.0370P)²+0.1001P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0716
_refine_ls_wR_factor_ref         0.0781
_reflns_Friedel_coverage         0.900
_reflns_Friedel_fraction_full    0.998
_reflns_Friedel_fraction_max     0.998
_reflns_number_gt                2633
_reflns_number_total             3349
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d3cc03160h2.cif
_cod_data_source_block           1e
_cod_depositor_comments          'Adding full bibliography for 7132588.cif.'
_cod_original_cell_volume        1461.2(7)
_cod_database_code               7132588
_shelx_shelxl_version_number     2018/3
_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.
;
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 N1(H1), C7(H7), C11(H11), C10(H10)
2.b Secondary CH2 refined with riding coordinates:
 C13(H13A,H13B), C9(H9A,H9B), C14(H14A,H14B)
2.c Idealised Me refined as rotating group:
 C12(H12A,H12B,H12C), C1(H1A,H1B,H1C), C2(H2A,H2B,H2C)
;
_olex2_submission_special_instructions 'No special instructions were received'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, z+1/2'
'x+1/2, -y, z'
'-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
O4 O 0.49732(9) 0.9232(2) 0.47116(14) 0.0458(5) Uani 1 1 d . . . . .
O2 O 0.42504(8) 1.0169(2) 0.31994(14) 0.0352(4) Uani 1 1 d . . . . .
O1 O 0.29782(8) 0.9260(2) 0.29847(14) 0.0382(4) Uani 1 1 d . . . . .
O3 O 0.24438(9) 0.7355(2) 0.42498(16) 0.0421(4) Uani 1 1 d . . . . .
N1 N 0.37176(10) 0.7554(2) 0.76615(16) 0.0305(4) Uani 1 1 d . . . . .
H1 H 0.332554 0.755581 0.829840 0.037 Uiso 1 1 calc R . . . .
O6 O 0.39572(10) 0.3888(2) 0.74163(19) 0.0543(5) Uani 1 1 d . . . . .
C6 C 0.30446(12) 0.8141(3) 0.39541(19) 0.0315(5) Uani 1 1 d . . . . .
C4 C 0.43626(12) 0.9095(3) 0.41903(19) 0.0308(5) Uani 1 1 d . . . . .
O5 O 0.38460(14) 0.4304(3) 0.3874(2) 0.0757(7) Uani 1 1 d . . . . .
C5 C 0.37448(12) 0.7995(3) 0.45263(19) 0.0291(5) Uani 1 1 d . . . . .
C7 C 0.38580(12) 0.6554(3) 0.54343(19) 0.0304(5) Uani 1 1 d . . . . .
H7 H 0.440100 0.652501 0.565724 0.036 Uiso 1 1 calc R . . . .
C12 C 0.38776(14) 0.9443(3) 0.7375(2) 0.0404(6) Uani 1 1 d . . . . .
H12A H 0.427211 0.951299 0.676961 0.061 Uiso 1 1 calc GR . . . .
H12B H 0.404312 1.003847 0.809805 0.061 Uiso 1 1 calc GR . . . .
H12C H 0.342036 0.999104 0.707312 0.061 Uiso 1 1 calc GR . . . .
C11 C 0.33831(11) 0.6564(3) 0.6610(2) 0.0296(5) Uani 1 1 d . . . . .
H11 H 0.288117 0.707441 0.642558 0.036 Uiso 1 1 calc R . . . .
C3 C 0.36819(12) 0.9635(3) 0.2345(2) 0.0344(5) Uani 1 1 d . . . . .
C13 C 0.43999(13) 0.6661(3) 0.8190(2) 0.0421(6) Uani 1 1 d . . . . .
H13A H 0.456028 0.726718 0.892228 0.050 Uiso 1 1 calc R . . . .
H13B H 0.481988 0.669186 0.761374 0.050 Uiso 1 1 calc R . . . .
C1 C 0.39398(14) 0.8042(4) 0.1647(2) 0.0456(6) Uani 1 1 d . . . . .
H1A H 0.442035 0.828770 0.125889 0.068 Uiso 1 1 calc GR . . . .
H1B H 0.356429 0.775515 0.104145 0.068 Uiso 1 1 calc GR . . . .
H1C H 0.399947 0.706735 0.219294 0.068 Uiso 1 1 calc GR . . . .
C10 C 0.32661(15) 0.4628(3) 0.6943(2) 0.0440(6) Uani 1 1 d . . . . .
H10 H 0.283025 0.445597 0.749062 0.053 Uiso 1 1 calc R . . . .
C9 C 0.31435(17) 0.3765(4) 0.5723(3) 0.0520(7) Uani 1 1 d . . . . .
H9A H 0.328971 0.253449 0.574749 0.062 Uiso 1 1 calc R . . . .
H9B H 0.261179 0.385023 0.547574 0.062 Uiso 1 1 calc R . . . .
C8 C 0.36495(15) 0.4775(3) 0.4874(3) 0.0446(6) Uani 1 1 d . . . . .
C2 C 0.35240(16) 1.1188(4) 0.1554(3) 0.0506(7) Uani 1 1 d . . . . .
H2A H 0.336565 1.216397 0.204759 0.076 Uiso 1 1 calc GR . . . .
H2B H 0.312474 1.090160 0.098800 0.076 Uiso 1 1 calc GR . . . .
H2C H 0.397991 1.149845 0.111649 0.076 Uiso 1 1 calc GR . . . .
C14 C 0.42008(17) 0.4790(4) 0.8482(3) 0.0566(8) Uani 1 1 d . . . . .
H14A H 0.464452 0.420097 0.882242 0.068 Uiso 1 1 calc R . . . .
H14B H 0.379536 0.476425 0.908422 0.068 Uiso 1 1 calc R . . . .
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
C4 O2 C3 116.91(16) . . ?
C6 O1 C3 115.46(16) . . ?
C12 N1 C11 113.06(17) . . ?
C13 N1 C12 111.72(17) . . ?
C13 N1 C11 112.61(18) . . ?
C14 O6 C10 111.3(2) . . ?
O1 C6 C5 118.73(18) . . ?
O3 C6 O1 115.36(19) . . ?
O3 C6 C5 125.9(2) . . ?
O4 C4 O2 116.64(19) . . ?
O4 C4 C5 126.6(2) . . ?
O2 C4 C5 116.68(19) . . ?
C6 C5 C4 120.62(19) . . ?
C6 C5 C7 118.75(19) . . ?
C4 C5 C7 120.44(19) . . ?
C5 C7 C11 119.17(18) . . ?
C5 C7 C8 110.23(19) . . ?
C8 C7 C11 102.46(18) . . ?
N1 C11 C7 116.25(17) . . ?
N1 C11 C10 110.49(19) . . ?
C10 C11 C7 105.58(19) . . ?
O2 C3 O1 109.12(18) . . ?
O2 C3 C1 110.96(18) . . ?
O2 C3 C2 106.7(2) . . ?
O1 C3 C1 110.21(19) . . ?
O1 C3 C2 106.44(19) . . ?
C2 C3 C1 113.2(2) . . ?
N1 C13 C14 109.31(19) . . ?
O6 C10 C11 110.63(19) . . ?
O6 C10 C9 105.9(2) . . ?
C9 C10 C11 102.9(2) . . ?
C8 C9 C10 104.4(2) . . ?
O5 C8 C7 124.2(2) . . ?
O5 C8 C9 125.8(2) . . ?
C9 C8 C7 110.0(2) . . ?
O6 C14 C13 110.4(2) . . ?
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
O4 C4 1.216(3) . ?
O2 C4 1.376(3) . ?
O2 C3 1.426(3) . ?
O1 C6 1.369(3) . ?
O1 C3 1.445(3) . ?
O3 C6 1.251(3) . ?
N1 C12 1.496(3) . ?
N1 C11 1.499(3) . ?
N1 C13 1.490(3) . ?
O6 C10 1.430(3) . ?
O6 C14 1.424(4) . ?
C6 C5 1.380(3) . ?
C4 C5 1.414(3) . ?
O5 C8 1.207(3) . ?
C5 C7 1.496(3) . ?
C7 C11 1.537(3) . ?
C7 C8 1.530(4) . ?
C11 C10 1.530(3) . ?
C3 C1 1.503(4) . ?
C3 C2 1.493(4) . ?
C13 C14 1.499(4) . ?
C10 C9 1.510(4) . ?
C9 C8 1.498(4) . ?
