#------------------------------------------------------------------------------
#$Date: 2025-08-05 01:18:04 +0300 (Tue, 05 Aug 2025) $
#$Revision: 301456 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/57/53/1575309.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_1575309
loop_
_publ_author_name
'Bera, Satyajit'
'Bhunia, Supriya'
'Dolai, Anirban'
'Box, Sk Majid'
'Das, Arpan'
'Samanta, Subhas'
_publ_section_title
;
 Arylpyrrolylidene-Indanones as Readily Synthesized Photoswitches Offering
 Dual- and Single-Color Fluorescence Toggling with Nearly Quantitative E/Z
 Isomerization under Visible Light
;
_journal_name_full               'Chemical Science'
_journal_paper_doi               10.1039/D5SC04551G
_journal_year                    2025
_chemical_formula_moiety         'C33 H25 N O2'
_chemical_formula_sum            'C33 H25 N O2'
_chemical_formula_weight         467.54
_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             2024-02-19
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2025-05-12 deposited with the CCDC.	2025-08-04 downloaded from the CCDC.
;
_cell_angle_alpha                103.318(5)
_cell_angle_beta                 104.698(5)
_cell_angle_gamma                109.450(5)
_cell_formula_units_Z            24
_cell_length_a                   10.405(2)
_cell_length_b                   11.265(2)
_cell_length_c                   11.901(2)
_cell_measurement_reflns_used    9390
_cell_measurement_temperature    130(2)
_cell_measurement_theta_max      67.01
_cell_measurement_theta_min      7.88
_cell_volume                     1194.1(4)
_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_temperature      130.0
_diffrn_measured_fraction_theta_full 0.933
_diffrn_measured_fraction_theta_max 0.897
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0599
_diffrn_reflns_av_unetI/netI     0.0475
_diffrn_reflns_Laue_measured_fraction_full 0.933
_diffrn_reflns_Laue_measured_fraction_max 0.897
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            25838
_diffrn_reflns_point_group_measured_fraction_full 0.933
_diffrn_reflns_point_group_measured_fraction_max 0.897
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         75.167
_diffrn_reflns_theta_min         10.211
_exptl_absorpt_coefficient_mu    0.630
_exptl_absorpt_correction_T_max  0.7528
_exptl_absorpt_correction_T_min  0.4208
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            red
_exptl_crystal_density_diffrn    1.300
_exptl_crystal_description       BLOCK
_exptl_crystal_F_000             492
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.421
_refine_diff_density_min         -0.438
_refine_diff_density_rms         0.104
_refine_ls_extinction_coef       0.123(14)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_goodness_of_fit_ref   1.053
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     327
_refine_ls_number_reflns         4411
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.053
_refine_ls_R_factor_all          0.0844
_refine_ls_R_factor_gt           0.0801
_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)+(0.1833P)²+0.2574P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2222
_refine_ls_wR_factor_ref         0.2289
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4186
_reflns_number_total             4411
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d5sc04551g2.cif
_cod_data_source_block           sb
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_exptl_absorpt_correction_type' value 'None' was changed
to 'none' in accordance with the
/home/data/users/saulius/crontab/automatic-downloads/rss-feeds/RSC/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 last updated on
2011-04-26.

Automatic conversion script
Id: cif_fix_values 8170 2020-07-09 18:12:32Z antanas 
;
_cod_database_code               1575309
_shelx_shelxl_version_number     2014/7
_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 N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 N1(H1), C7(H7), C10(H10), C33(H33), C12(H12), C19(H19), C9(H9), C4(H4),
 C23(H23), C29(H29), C32(H32), C3(H3), C31(H31), C25(H25), C27(H27), C6(H6),
 C30(H30), C16(H16), C17(H17), C24(H24), C18(H18), C26(H26)
2.b Idealised Me refined as rotating group:
 C1(H1a,H1b,H1c)
;
_olex2_submission_special_instructions 'No special instructions were received'
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
O2 O 0.51989(12) 0.41512(11) 0.60051(11) 0.0260(4) Uani 1 1 d . . . . .
O1 O 0.91929(14) 0.81076(13) 1.28165(12) 0.0330(4) Uani 1 1 d . . . . .
N1 N 0.81092(14) 0.50499(13) 0.71355(13) 0.0225(4) Uani 1 1 d . . . . .
H1 H 0.7219 0.4916 0.7114 0.027 Uiso 1 1 calc R . . . .
C14 C 0.49378(17) 0.34063(15) 0.49528(15) 0.0216(4) Uani 1 1 d . . . . .
C8 C 0.93509(17) 0.58005(16) 0.81574(15) 0.0237(4) Uani 1 1 d . . . . .
C13 C 0.59651(17) 0.31281(15) 0.44133(14) 0.0208(4) Uani 1 1 d . . . . .
C11 C 0.84535(17) 0.45331(16) 0.61453(15) 0.0233(4) Uani 1 1 d . . . . .
C7 C 0.81414(17) 0.72673(16) 1.06555(16) 0.0263(4) Uani 1 1 d . . . . .
H7 H 0.7333 0.7450 1.0729 0.032 Uiso 1 1 calc R . . . .
C15 C 0.34662(17) 0.26025(15) 0.39980(16) 0.0230(4) Uani 1 1 d . . . . .
C21 C 0.51294(16) 0.20822(15) 0.30960(15) 0.0212(4) Uani 1 1 d . . . . .
C5 C 0.93295(17) 0.64336(16) 0.93613(15) 0.0236(4) Uani 1 1 d . . . . .
C28 C 0.54376(17) 0.08342(15) 0.30811(14) 0.0224(4) Uani 1 1 d . . . . .
C22 C 0.54670(16) 0.26323(15) 0.20830(15) 0.0225(4) Uani 1 1 d . . . . .
C10 C 0.99784(18) 0.49872(17) 0.65681(16) 0.0268(4) Uani 1 1 d . . . . .
H10 H 1.0535 0.4792 0.6090 0.032 Uiso 1 1 calc R . . . .
C20 C 0.35424(17) 0.18275(16) 0.29502(16) 0.0230(4) Uani 1 1 d . . . . .
C33 C 0.67069(17) 0.07754(16) 0.29210(15) 0.0255(4) Uani 1 1 d . . . . .
H33 H 0.7341 0.1479 0.2747 0.031 Uiso 1 1 calc R . . . .
C12 C 0.74546(17) 0.36493(15) 0.49397(15) 0.0220(4) Uani 1 1 d . . . . .
H12 H 0.7909 0.3368 0.4397 0.026 Uiso 1 1 calc R . . . .
C19 C 0.22725(18) 0.09722(17) 0.19284(17) 0.0277(4) Uani 1 1 d . . . . .
H19 H 0.2311 0.0428 0.1209 0.033 Uiso 1 1 calc R . . . .
C9 C 1.05289(18) 0.57739(18) 0.78129(16) 0.0280(4) Uani 1 1 d . . . . .
H9 H 1.1530 0.6215 0.8336 0.034 Uiso 1 1 calc R . . . .
C4 C 1.05194(18) 0.67875(17) 1.04401(16) 0.0265(4) Uani 1 1 d . . . . .
H4 H 1.1343 0.6633 1.0369 0.032 Uiso 1 1 calc R . . . .
C23 C 0.58518(17) 0.39911(17) 0.22509(16) 0.0255(4) Uani 1 1 d . . . . .
H23 H 0.5973 0.4587 0.3018 0.031 Uiso 1 1 calc R . . . .
C29 C 0.45232(18) -0.02240(17) 0.33207(16) 0.0262(4) Uani 1 1 d . . . . .
H29 H 0.3656 -0.0205 0.3430 0.031 Uiso 1 1 calc R . . . .
C32 C 0.70502(18) -0.02973(17) 0.30136(16) 0.0280(4) Uani 1 1 d . . . . .
H32 H 0.7919 -0.0319 0.2910 0.034 Uiso 1 1 calc R . . . .
C3 C 1.05259(18) 0.73541(17) 1.16012(16) 0.0277(4) Uani 1 1 d . . . . .
H3 H 1.1345 0.7585 1.2318 0.033 Uiso 1 1 calc R . . . .
C2 C 0.93199(18) 0.75857(16) 1.17160(16) 0.0256(4) Uani 1 1 d . . . . .
C31 C 0.6125(2) -0.13428(17) 0.32583(16) 0.0295(4) Uani 1 1 d . . . . .
H31 H 0.6362 -0.2075 0.3325 0.035 Uiso 1 1 calc R . . . .
C25 C 0.58895(18) 0.36219(19) 0.01803(17) 0.0304(4) Uani 1 1 d . . . . .
H25 H 0.6038 0.3958 -0.0461 0.036 Uiso 1 1 calc R . . . .
C27 C 0.52732(18) 0.17798(17) 0.09420(16) 0.0275(4) Uani 1 1 d . . . . .
H27 H 0.4980 0.0848 0.0801 0.033 Uiso 1 1 calc R . . . .
C6 C 0.81374(17) 0.66891(16) 0.94996(16) 0.0254(4) Uani 1 1 d . . . . .
H6 H 0.7316 0.6460 0.8786 0.031 Uiso 1 1 calc R . . . .
C30 C 0.4857(2) -0.13048(18) 0.34030(17) 0.0306(4) Uani 1 1 d . . . . .
H30 H 0.4214 -0.2019 0.3559 0.037 Uiso 1 1 calc R . . . .
C16 C 0.21314(18) 0.25685(17) 0.40649(18) 0.0279(4) Uani 1 1 d . . . . .
H16 H 0.2090 0.3103 0.4788 0.034 Uiso 1 1 calc R . . . .
C17 C 0.08767(18) 0.17354(18) 0.30483(19) 0.0327(5) Uani 1 1 d . . . . .
H17 H -0.0042 0.1703 0.3065 0.039 Uiso 1 1 calc R . . . .
C24 C 0.60593(18) 0.44810(18) 0.13109(18) 0.0294(4) Uani 1 1 d . . . . .
H24 H 0.6319 0.5407 0.1439 0.035 Uiso 1 1 calc R . . . .
C18 C 0.09478(18) 0.09430(18) 0.19991(18) 0.0321(5) Uani 1 1 d . . . . .
H18 H 0.0070 0.0368 0.1314 0.039 Uiso 1 1 calc R . . . .
C26 C 0.55023(19) 0.22724(19) 0.00031(16) 0.0303(4) Uani 1 1 d . . . . .
H26 H 0.5392 0.1680 -0.0761 0.036 Uiso 1 1 calc R . . . .
C1 C 1.0433(2) 0.8598(2) 1.39177(17) 0.0354(5) Uani 1 1 d . . . . .
H1A H 1.1238 0.9333 1.3883 0.053 Uiso 1 1 calc GR . . . .
H1B H 1.0730 0.7872 1.3995 0.053 Uiso 1 1 calc GR . . . .
H1C H 1.0186 0.8927 1.4634 0.053 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_
_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 O1 C1 118.06(14) . . ?
C8 N1 H1 125.0 . . ?
C8 N1 C11 110.06(14) . . ?
C11 N1 H1 125.0 . . ?
O2 C14 C13 128.53(14) . . ?
O2 C14 C15 124.78(15) . . ?
C13 C14 C15 106.68(13) . . ?
N1 C8 C5 122.73(15) . . ?
N1 C8 C9 107.47(14) . . ?
C9 C8 C5 129.76(14) . . ?
C14 C13 C21 110.03(13) . . ?
C12 C13 C14 128.30(15) . . ?
C12 C13 C21 121.66(14) . . ?
N1 C11 C10 106.84(14) . . ?
N1 C11 C12 126.77(15) . . ?
C10 C11 C12 126.31(16) . . ?
C2 C7 H7 119.7 . . ?
C6 C7 H7 119.7 . . ?
C6 C7 C2 120.58(15) . . ?
C20 C15 C14 110.48(14) . . ?
C20 C15 C16 121.57(15) . . ?
C16 C15 C14 127.95(16) . . ?
C28 C21 C13 108.03(12) . . ?
C28 C21 C22 113.00(13) . . ?
C22 C21 C13 113.36(12) . . ?
C20 C21 C13 101.44(12) . . ?
C20 C21 C28 112.81(12) . . ?
C20 C21 C22 107.70(12) . . ?
C4 C5 C8 119.96(15) . . ?
C6 C5 C8 122.45(14) . . ?
C6 C5 C4 117.58(15) . . ?
C33 C28 C21 120.78(14) . . ?
C29 C28 C21 121.03(14) . . ?
C29 C28 C33 118.01(15) . . ?
C23 C22 C21 120.33(14) . . ?
C27 C22 C21 121.21(14) . . ?
C27 C22 C23 118.22(16) . . ?
C11 C10 H10 126.1 . . ?
C9 C10 C11 107.75(15) . . ?
C9 C10 H10 126.1 . . ?
C15 C20 C21 111.32(14) . . ?
C15 C20 C19 120.41(15) . . ?
C19 C20 C21 128.26(15) . . ?
C28 C33 H33 119.6 . . ?
C32 C33 C28 120.88(16) . . ?
C32 C33 H33 119.6 . . ?
C13 C12 C11 132.29(16) . . ?
C13 C12 H12 113.9 . . ?
C11 C12 H12 113.9 . . ?
C20 C19 H19 121.1 . . ?
C18 C19 C20 117.80(17) . . ?
C18 C19 H19 121.1 . . ?
C8 C9 H9 126.1 . . ?
C10 C9 C8 107.86(15) . . ?
C10 C9 H9 126.1 . . ?
C5 C4 H4 119.1 . . ?
C3 C4 C5 121.83(15) . . ?
C3 C4 H4 119.1 . . ?
C22 C23 H23 119.6 . . ?
C24 C23 C22 120.85(16) . . ?
C24 C23 H23 119.6 . . ?
C28 C29 H29 119.4 . . ?
C30 C29 C28 121.26(16) . . ?
C30 C29 H29 119.4 . . ?
C33 C32 H32 119.9 . . ?
C33 C32 C31 120.26(16) . . ?
C31 C32 H32 119.9 . . ?
C4 C3 H3 120.2 . . ?
C4 C3 C2 119.54(15) . . ?
C2 C3 H3 120.2 . . ?
O1 C2 C7 116.00(15) . . ?
O1 C2 C3 124.50(15) . . ?
C7 C2 C3 119.50(16) . . ?
C32 C31 H31 120.3 . . ?
C30 C31 C32 119.42(15) . . ?
C30 C31 H31 120.3 . . ?
C24 C25 H25 120.4 . . ?
C26 C25 H25 120.4 . . ?
C26 C25 C24 119.18(17) . . ?
C22 C27 H27 119.5 . . ?
C22 C27 C26 121.03(16) . . ?
C26 C27 H27 119.5 . . ?
C7 C6 C5 120.95(15) . . ?
C7 C6 H6 119.5 . . ?
C5 C6 H6 119.5 . . ?
C29 C30 H30 119.9 . . ?
C31 C30 C29 120.17(17) . . ?
C31 C30 H30 119.9 . . ?
C15 C16 H16 121.0 . . ?
C17 C16 C15 118.04(17) . . ?
C17 C16 H16 121.0 . . ?
C16 C17 H17 119.7 . . ?
C16 C17 C18 120.53(16) . . ?
C18 C17 H17 119.7 . . ?
C23 C24 C25 120.41(16) . . ?
C23 C24 H24 119.8 . . ?
C25 C24 H24 119.8 . . ?
C19 C18 C17 121.64(16) . . ?
C19 C18 H18 119.2 . . ?
C17 C18 H18 119.2 . . ?
C25 C26 C27 120.28(16) . . ?
C25 C26 H26 119.9 . . ?
C27 C26 H26 119.9 . . ?
O1 C1 H1A 109.5 . . ?
O1 C1 H1B 109.5 . . ?
O1 C1 H1C 109.5 . . ?
H1A C1 H1B 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 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
O2 C14 1.240(2) . ?
O1 C2 1.365(2) . ?
O1 C1 1.422(2) . ?
N1 H1 0.8800 . ?
N1 C8 1.366(2) . ?
N1 C11 1.376(2) . ?
C14 C13 1.460(2) . ?
C14 C15 1.475(2) . ?
C8 C5 1.455(2) . ?
C8 C9 1.395(2) . ?
C13 C21 1.542(2) . ?
C13 C12 1.368(2) . ?
C11 C10 1.403(2) . ?
C11 C12 1.423(2) . ?
C7 H7 0.9500 . ?
C7 C2 1.392(2) . ?
C7 C6 1.378(2) . ?
C15 C20 1.385(2) . ?
C15 C16 1.400(2) . ?
C21 C28 1.540(2) . ?
C21 C22 1.541(2) . ?
C21 C20 1.535(2) . ?
C5 C4 1.403(2) . ?
C5 C6 1.403(2) . ?
C28 C33 1.402(2) . ?
C28 C29 1.395(2) . ?
C22 C23 1.398(2) . ?
C22 C27 1.392(2) . ?
C10 H10 0.9500 . ?
C10 C9 1.391(2) . ?
C20 C19 1.396(2) . ?
C33 H33 0.9500 . ?
C33 C32 1.389(2) . ?
C12 H12 0.9500 . ?
C19 H19 0.9500 . ?
C19 C18 1.392(2) . ?
C9 H9 0.9500 . ?
C4 H4 0.9500 . ?
C4 C3 1.379(2) . ?
C23 H23 0.9500 . ?
C23 C24 1.389(3) . ?
C29 H29 0.9500 . ?
C29 C30 1.390(2) . ?
C32 H32 0.9500 . ?
C32 C31 1.394(3) . ?
C3 H3 0.9500 . ?
C3 C2 1.396(2) . ?
C31 H31 0.9500 . ?
C31 C30 1.387(3) . ?
C25 H25 0.9500 . ?
C25 C24 1.394(3) . ?
C25 C26 1.385(3) . ?
C27 H27 0.9500 . ?
C27 C26 1.395(3) . ?
C6 H6 0.9500 . ?
C30 H30 0.9500 . ?
C16 H16 0.9500 . ?
C16 C17 1.381(3) . ?
C17 H17 0.9500 . ?
C17 C18 1.392(3) . ?
C24 H24 0.9500 . ?
C18 H18 0.9500 . ?
C26 H26 0.9500 . ?
C1 H1A 0.9800 . ?
C1 H1B 0.9800 . ?
C1 H1C 0.9800 . ?
