#------------------------------------------------------------------------------
#$Date: 2024-01-06 09:38:50 +0200 (Sat, 06 Jan 2024) $
#$Revision: 288767 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/57/02/1570239.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_1570239
loop_
_publ_author_name
'Ye, Changqing'
'Huang, Rui'
'Chiou, Mong-Feng'
'Wang, Bo'
'Li, Daliang'
'Bao, Hongli'
_publ_section_title
;
 Synthesis of a new fluorophore: wavelength-tunable
 bisbenzo[f]isoindolylidenes.
;
_journal_issue                   45
_journal_name_full               'Chemical science'
_journal_page_first              13151
_journal_page_last               13158
_journal_paper_doi               10.1039/d3sc04445a
_journal_volume                  14
_journal_year                    2023
_chemical_formula_moiety         'C36 H22 N2'
_chemical_formula_sum            'C36 H22 N2'
_chemical_formula_weight         482.55
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2019-11-11
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2021-12-13 deposited with the CCDC.	2023-11-01 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 101.414(6)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   12.4695(8)
_cell_length_b                   5.8013(3)
_cell_length_c                   17.3780(10)
_cell_measurement_reflns_used    2426
_cell_measurement_temperature    299.22(19)
_cell_measurement_theta_max      57.6510
_cell_measurement_theta_min      3.4530
_cell_volume                     1232.25(13)
_computing_cell_refinement       'CrysAlisPro 1.171.40.59a (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.59a (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.59a (Rigaku OD, 2019)'
_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_environment      air
_diffrn_ambient_temperature      299.22(19)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.964
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -71.00 -39.00   0.50    0.60    --   -1.41 -18.00  48.00   64
  2  ω    -34.00  14.00   0.50    0.60    --   -1.41 -18.00  48.00   96
  3  ω      1.00  26.00   0.50    2.40    --   72.34 -18.00  48.00   50
  4  ω      0.00  43.00   0.50    2.40    --   72.34 -38.00  90.00   86
  5  ω      1.00  63.00   0.50    2.40    --   72.34 -57.00-120.00  124
  6  ω     68.00  96.00   0.50    2.40    --   72.34 -77.00-120.00   56
  7  ω     43.00 108.00   0.50    2.40    --   72.34-125.00-120.00  130
  8  ω     17.00  59.00   0.50    2.40    --   72.34 -77.00-120.00   84
  9  ω     57.00 136.00   0.50    2.40    --   72.34  18.00-143.00  158
 10  ω     40.00  70.00   0.50    0.60    --   -1.41  38.00-150.00   60
 11  ω     20.00  45.00   0.50    0.60    --   -1.41  18.00-143.00   50
 12  ω     10.00  35.00   0.50    0.60    --   -1.41  38.00-150.00   50
 13  ω    -26.00  -1.00   0.50    2.40    --  -75.15  18.00-143.00   50
 14  ω    -26.00  -1.00   0.50    2.40    --  -75.15  19.00-180.00   50
 15  ω    -42.00  -5.00   0.50    2.40    --  -75.15  38.00 -30.00   74
 16  ω    -28.00  -2.00   0.50    2.40    --  -75.15  38.00   0.00   52
 17  ω    -66.00  -6.00   0.50    2.40    --  -75.15  57.00   0.00  120
 18  ω   -146.00 -71.00   0.50    2.40    --  -75.15 -18.00  48.00  150
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'ROD, Synergy Custom system, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0348030000
_diffrn_orient_matrix_UB_12      0.0363363000
_diffrn_orient_matrix_UB_13      -0.0769642000
_diffrn_orient_matrix_UB_21      -0.1031689000
_diffrn_orient_matrix_UB_22      -0.0389979000
_diffrn_orient_matrix_UB_23      0.0078963000
_diffrn_orient_matrix_UB_31      -0.0122712000
_diffrn_orient_matrix_UB_32      0.2246143000
_diffrn_orient_matrix_UB_33      0.0138182000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           GaK\a
_diffrn_radiation_wavelength     1.3405
_diffrn_reflns_av_R_equivalents  0.0691
_diffrn_reflns_av_unetI/netI     0.0603
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.964
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -3
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            9039
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.964
_diffrn_reflns_theta_full        53.543
_diffrn_reflns_theta_max         60.545
_diffrn_reflns_theta_min         3.488
_diffrn_source                   'micro-focus metaljet'
_exptl_absorpt_coefficient_mu    0.375
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.52010
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.40.59a (Rigaku Oxford Diffraction, 2019)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'dark orange'
_exptl_crystal_colour_modifier   dark
_exptl_crystal_colour_primary    orange
_exptl_crystal_density_diffrn    1.301
_exptl_crystal_description       needle
_exptl_crystal_F_000             504
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.223
_refine_diff_density_min         -0.181
_refine_diff_density_rms         0.044
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.015
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     172
_refine_ls_number_reflns         2730
_refine_ls_number_restraints     36
_refine_ls_restrained_S_all      1.009
_refine_ls_R_factor_all          0.0937
_refine_ls_R_factor_gt           0.0617
_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)+(0.1205P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1756
_refine_ls_wR_factor_ref         0.2001
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1785
_reflns_number_total             2730
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d3sc04445a2.cif
_cod_data_source_block           ycq-20191111
_cod_depositor_comments
'Adding full bibliography for 1570237--1570240.cif.'
_cod_database_code               1570239
_shelx_shelxl_version_number     2017/1
_chemical_oxdiff_formula         CHN
_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.
;
_diffrn_oxdiff_digest_frames
;
01e5f25597962cb53dc4c9cc56247b967d00030662d
;
_diffrn_oxdiff_digest_hkl
;
01e9d0dd0db28c3d29d169c03e3c7c0009f8b2
;
_reflns_odcompleteness_completeness 99.53
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     56.82
_olex2_refinement_description
;
1. Others
 Fixed Uiso: H009(0.068) H00A(0.066) H00B(0.073) H00C(0.08) H00D(0.078)
 H00E(0.079) H00F(0.084) H00G(0.092) H00H(0.09) H00I(0.098) H00J(0.107)
 Fixed X: H009(0.486267) H00A(0.691839) H00B(0.685318) H00C(0.635799)
 H00D(0.639568) H00E(0.488196) H00F(0.537629) H00G(0.738356) H00H(0.861729)
 H00I(0.792933) H00J(0.889775)
 Fixed Y: H009(1.083192) H00A(0.401316) H00B(0.373499) H00C(0.521899)
 H00D(0.469046) H00E(1.05491) H00F(0.864299) H00G(0.18528) H00H(-0.032764)
 H00I(0.328876) H00J(0.042151)
 Fixed Z: H009(0.33321) H00A(0.374449) H00B(0.230933) H00C(0.108102)
 H00D(0.655223) H00E(0.18985) H00F(0.087388) H00G(0.728876) H00H(0.678811)
 H00I(0.480108) H00J(0.554267)
;
_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
;
_oxdiff_exptl_absorpt_empirical_full_max 2.140
_oxdiff_exptl_absorpt_empirical_full_min 0.377
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, 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
N001 N 0.58515(14) 0.7597(3) 0.54721(10) 0.0576(5) Uani 1 1 d . . . . .
C002 C 0.70396(17) 0.4294(3) 0.55896(12) 0.0552(5) Uani 1 1 d . U . . .
C003 C 0.63888(17) 0.6099(3) 0.51284(12) 0.0543(5) Uani 1 1 d . . . . .
C004 C 0.62310(17) 0.6530(3) 0.42786(11) 0.0525(5) Uani 1 1 d . . . . .
C005 C 0.55936(17) 0.8353(3) 0.27680(12) 0.0549(5) Uani 1 1 d . . . . .
C006 C 0.55857(17) 0.8564(3) 0.41468(12) 0.0540(5) Uani 1 1 d . . . . .
C007 C 0.53259(18) 0.9149(3) 0.49058(13) 0.0564(5) Uani 1 1 d . . . . .
C008 C 0.61904(17) 0.6253(3) 0.28909(12) 0.0542(5) Uani 1 1 d . . . . .
C009 C 0.52752(17) 0.9486(3) 0.34096(12) 0.0570(5) Uani 1 1 d . . . . .
H009 H 0.486267 1.083192 0.333210 0.068 Uiso 1 1 calc R . . . .
C00A C 0.65151(17) 0.5370(3) 0.36587(12) 0.0553(5) Uani 1 1 d . . . . .
H00A H 0.691839 0.401316 0.374449 0.066 Uiso 1 1 calc R . . . .
C00B C 0.64636(19) 0.5111(3) 0.22351(12) 0.0605(6) Uani 1 1 d . . . . .
H00B H 0.685318 0.373499 0.230933 0.073 Uiso 1 1 calc R . . . .
C00C C 0.6167(2) 0.5988(4) 0.15039(14) 0.0669(6) Uani 1 1 d . . . . .
H00C H 0.635799 0.521899 0.108102 0.080 Uiso 1 1 calc R . . . .
C00D C 0.6898(2) 0.3835(3) 0.63410(13) 0.0651(6) Uani 1 1 d . U . . .
H00D H 0.639568 0.469046 0.655223 0.078 Uiso 1 1 calc R . . . .
C00E C 0.5286(2) 0.9195(3) 0.19919(13) 0.0656(6) Uani 1 1 d . . . . .
H00E H 0.488196 1.054910 0.189850 0.079 Uiso 1 1 calc R . . . .
C00F C 0.5575(2) 0.8050(4) 0.13793(14) 0.0702(6) Uani 1 1 d . . . . .
H00F H 0.537629 0.864299 0.087388 0.084 Uiso 1 1 calc R . . . .
C00G C 0.7489(2) 0.2130(4) 0.67819(15) 0.0763(7) Uani 1 1 d . U . . .
H00G H 0.738356 0.185280 0.728876 0.092 Uiso 1 1 calc R . . . .
C00H C 0.8228(2) 0.0839(4) 0.64883(15) 0.0753(7) Uani 1 1 d . U . . .
H00H H 0.861729 -0.032764 0.678811 0.090 Uiso 1 1 calc R . . . .
C00I C 0.7807(2) 0.2996(4) 0.53028(15) 0.0813(8) Uani 1 1 d . U . . .
H00I H 0.792933 0.328876 0.480108 0.098 Uiso 1 1 calc R . . . .
C00J C 0.8391(2) 0.1282(5) 0.57473(16) 0.0890(9) Uani 1 1 d . U . . .
H00J H 0.889775 0.042151 0.554267 0.107 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 0.0147 0.0070 '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 0.0253 0.0135 '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
C003 N001 C007 108.48(17) . . ?
C00D C002 C003 119.77(18) . . ?
C00D C002 C00I 117.6(2) . . ?
C00I C002 C003 122.65(19) . . ?
N001 C003 C002 120.19(18) . . ?
N001 C003 C004 111.45(17) . . ?
C002 C003 C004 128.36(16) . . ?
C006 C004 C003 105.16(15) . . ?
C00A C004 C003 134.36(18) . . ?
C00A C004 C006 120.37(18) . . ?
C009 C005 C008 119.94(18) . . ?
C00E C005 C008 118.31(17) . . ?
C00E C005 C009 121.67(19) . . ?
C004 C006 C007 105.51(17) . . ?
C009 C006 C004 121.37(16) . . ?
C009 C006 C007 132.96(19) . . ?
N001 C007 C006 109.24(16) . . ?
C007 C007 N001 121.2(2) 3_676 . ?
C007 C007 C006 129.6(3) 3_676 . ?
C00A C008 C005 119.79(17) . . ?
C00A C008 C00B 121.38(18) . . ?
C00B C008 C005 118.82(18) . . ?
C005 C009 H009 120.6 . . ?
C006 C009 C005 118.87(18) . . ?
C006 C009 H009 120.6 . . ?
C004 C00A C008 119.52(18) . . ?
C004 C00A H00A 120.2 . . ?
C008 C00A H00A 120.2 . . ?
C008 C00B H00B 119.5 . . ?
C00C C00B C008 121.05(19) . . ?
C00C C00B H00B 119.5 . . ?
C00B C00C H00C 119.8 . . ?
C00B C00C C00F 120.3(2) . . ?
C00F C00C H00C 119.8 . . ?
C002 C00D H00D 119.6 . . ?
C00G C00D C002 120.9(2) . . ?
C00G C00D H00D 119.6 . . ?
C005 C00E H00E 119.6 . . ?
C00F C00E C005 120.9(2) . . ?
C00F C00E H00E 119.6 . . ?
C00C C00F H00F 119.7 . . ?
C00E C00F C00C 120.6(2) . . ?
C00E C00F H00F 119.7 . . ?
C00D C00G H00G 119.5 . . ?
C00H C00G C00D 121.0(2) . . ?
C00H C00G H00G 119.5 . . ?
C00G C00H H00H 120.4 . . ?
C00G C00H C00J 119.1(2) . . ?
C00J C00H H00H 120.4 . . ?
C002 C00I H00I 119.4 . . ?
C00J C00I C002 121.1(2) . . ?
C00J C00I H00I 119.4 . . ?
C00H C00J C00I 120.3(2) . . ?
C00H C00J H00J 119.9 . . ?
C00I C00J H00J 119.9 . . ?
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
N001 C003 1.311(2) . ?
N001 C007 1.398(3) . ?
C002 C003 1.463(3) . ?
C002 C00D 1.378(3) . ?
C002 C00I 1.385(3) . ?
C003 C004 1.472(3) . ?
C004 C006 1.421(3) . ?
C004 C00A 1.375(2) . ?
C005 C008 1.422(3) . ?
C005 C009 1.417(3) . ?
C005 C00E 1.414(3) . ?
C006 C007 1.459(3) . ?
C006 C009 1.372(3) . ?
C007 C007 1.359(4) 3_676 ?
C008 C00A 1.412(3) . ?
C008 C00B 1.417(3) . ?
C009 H009 0.9300 . ?
C00A H00A 0.9300 . ?
C00B H00B 0.9300 . ?
C00B C00C 1.351(3) . ?
C00C H00C 0.9300 . ?
C00C C00F 1.400(3) . ?
C00D H00D 0.9300 . ?
C00D C00G 1.373(3) . ?
C00E H00E 0.9300 . ?
C00E C00F 1.362(3) . ?
C00F H00F 0.9300 . ?
C00G H00G 0.9300 . ?
C00G C00H 1.363(3) . ?
C00H H00H 0.9300 . ?
C00H C00J 1.367(3) . ?
C00I H00I 0.9300 . ?
C00I C00J 1.376(3) . ?
C00J H00J 0.9300 . ?
