#------------------------------------------------------------------------------
#$Date: 2021-09-06 12:30:27 +0200 (lun 06 de sep de 2021) $
#$Revision: 268678 $
#$URL: svn://www.crystallography.net/cod/cif/7/24/24/7242412.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_7242412
loop_
_publ_author_name
'Cao, Lifu'
'Tang, Baolei'
'Yu, Xu'
'Ye, Kaiqi'
'Zhang, Hongyu'
_publ_section_title
;
 Intense red emissive organic crystals with elastic bending ability and
 optical waveguiding behaviour
;
_journal_issue                   34
_journal_name_full               CrystEngComm
_journal_page_first              5758
_journal_page_last               5762
_journal_paper_doi               10.1039/D1CE00192B
_journal_volume                  23
_journal_year                    2021
_chemical_formula_moiety         'C26 H18 N4 O6'
_chemical_formula_sum            'C26 H18 N4 O6'
_chemical_formula_weight         482.44
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_audit_creation_date             2021-01-09
_audit_creation_method
;
Olex2 1.2
(compiled 2018.04.18 svn.r3501 for OlexSys, GUI svn.r5488)
;
_audit_update_record
;
2021-01-13 deposited with the CCDC.	2021-03-15 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 93.330(4)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   4.5740(5)
_cell_length_b                   10.4956(12)
_cell_length_c                   22.772(2)
_cell_measurement_reflns_used    9952
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      31.554
_cell_measurement_theta_min      2.641
_cell_volume                     1091.4(2)
_computing_cell_refinement       'SAINT V8.40A (?, 2016)'
_computing_data_reduction        'SAINT V8.40A (?, 2016)'
_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    'olex2.solve (Bourhis et al., 2015)'
_diffrn_ambient_temperature      100.0
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.996
_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  0.0960
_diffrn_reflns_av_unetI/netI     0.0453
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       33
_diffrn_reflns_limit_l_min       -33
_diffrn_reflns_number            56919
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         31.622
_diffrn_reflns_theta_min         2.641
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.107
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            red
_exptl_crystal_colour_primary    red
_exptl_crystal_density_diffrn    1.468
_exptl_crystal_description       needle
_exptl_crystal_F_000             500
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.09
_refine_diff_density_max         0.545
_refine_diff_density_min         -0.404
_refine_diff_density_rms         0.096
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.230
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     164
_refine_ls_number_reflns         3650
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.230
_refine_ls_R_factor_all          0.1312
_refine_ls_R_factor_gt           0.1045
_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)+(0.0354P)²+3.9843P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2135
_refine_ls_wR_factor_ref         0.2241
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2883
_reflns_number_total             3650
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d1ce00192b2.cif
_cod_data_source_block           1_CCDC1
_cod_depositor_comments
'Adding full bibliography for 7242411--7242412.cif.'
_cod_database_code               7242412
_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.
;
_shelx_estimated_absorpt_t_max   0.990
_shelx_estimated_absorpt_t_min   0.987
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C3(H3), C6(H6), C8(H8), C10(H10), C11(H11), C12(H12)
2.b Idealised Me refined as rotating group:
 C14(H14A,H14B,H14C)
;
_olex2_submission_special_instructions 'No special instructions were received'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -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
O1 O -0.1650(6) 0.4482(3) 0.25794(12) 0.0324(6) Uani 1 1 d . . . . .
O2 O -0.4617(6) 0.3014(3) 0.22441(12) 0.0327(6) Uani 1 1 d . . . . .
O3 O 0.8212(5) 0.5795(2) 0.38803(10) 0.0191(5) Uani 1 1 d . . . . .
N0AA N 0.4216(7) 0.1355(3) 0.53393(14) 0.0280(7) Uani 1 1 d . . . . .
N1 N -0.2681(6) 0.3404(3) 0.25937(12) 0.0202(5) Uani 1 1 d . . . . .
C2 C -0.1559(6) 0.2524(3) 0.30613(13) 0.0158(5) Uani 1 1 d . . . . .
C3 C 0.0591(6) 0.2980(3) 0.34602(13) 0.0157(5) Uani 1 1 d . . . . .
H3 H 0.1373 0.3811 0.3417 0.019 Uiso 1 1 calc R . . . .
C4 C 0.1594(6) 0.2201(3) 0.39278(12) 0.0132(5) Uani 1 1 d . . . . .
C5 C 0.3841(6) 0.2666(3) 0.43747(12) 0.0141(5) Uani 1 1 d . . . . .
C6 C 0.5486(6) 0.3722(3) 0.42918(13) 0.0137(5) Uani 1 1 d . . . . .
H6 H 0.5088 0.4129 0.3923 0.016 Uiso 1 1 calc R . . . .
C7 C 0.7747(6) 0.4344(3) 0.46665(12) 0.0130(5) Uani 1 1 d . . . . .
C8 C 1.1347(6) 0.6059(3) 0.47657(13) 0.0153(5) Uani 1 1 d . . . . .
H8 H 1.2256 0.6780 0.4602 0.018 Uiso 1 1 calc R . . . .
C9 C 0.9143(6) 0.5425(3) 0.44364(13) 0.0141(5) Uani 1 1 d . . . . .
C10 C 0.0348(6) 0.0988(3) 0.39737(14) 0.0176(6) Uani 1 1 d . . . . .
H10 H 0.0984 0.0449 0.4291 0.021 Uiso 1 1 calc R . . . .
C11 C -0.1803(7) 0.0557(3) 0.35645(14) 0.0201(6) Uani 1 1 d . . . . .
H11 H -0.2600 -0.0273 0.3604 0.024 Uiso 1 1 calc R . . . .
C12 C -0.2796(7) 0.1330(3) 0.30983(14) 0.0196(6) Uani 1 1 d . . . . .
H12 H -0.4268 0.1047 0.2817 0.024 Uiso 1 1 calc R . . . .
C13 C 0.4097(6) 0.1941(3) 0.49126(14) 0.0179(6) Uani 1 1 d . . . . .
C14 C 0.9898(7) 0.6747(3) 0.36028(14) 0.0223(6) Uani 1 1 d . . . . .
H14A H 0.9775 0.7553 0.3818 0.033 Uiso 1 1 calc GR . . . .
H14B H 0.9128 0.6867 0.3196 0.033 Uiso 1 1 calc GR . . . .
H14C H 1.1948 0.6474 0.3605 0.033 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 0.0033 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
C9 O3 C14 117.4(2) . . ?
O1 N1 C2 118.5(3) . . ?
O2 N1 O1 123.7(3) . . ?
O2 N1 C2 117.8(3) . . ?
C3 C2 N1 117.4(3) . . ?
C12 C2 N1 119.0(3) . . ?
C12 C2 C3 123.5(3) . . ?
C2 C3 H3 120.5 . . ?
C2 C3 C4 119.1(3) . . ?
C4 C3 H3 120.5 . . ?
C3 C4 C5 120.8(3) . . ?
C3 C4 C10 118.1(3) . . ?
C10 C4 C5 121.0(3) . . ?
C6 C5 C4 122.6(3) . . ?
C6 C5 C13 122.0(3) . . ?
C13 C5 C4 115.3(3) . . ?
C5 C6 H6 114.2 . . ?
C5 C6 C7 131.6(3) . . ?
C7 C6 H6 114.2 . . ?
C8 C7 C6 124.6(3) 3_766 . ?
C8 C7 C9 117.9(2) 3_766 . ?
C9 C7 C6 117.5(3) . . ?
C7 C8 H8 119.3 3_766 . ?
C9 C8 C7 121.3(3) . 3_766 ?
C9 C8 H8 119.3 . . ?
O3 C9 C7 116.5(2) . . ?
O3 C9 C8 122.7(3) . . ?
C8 C9 C7 120.8(3) . . ?
C4 C10 H10 119.3 . . ?
C11 C10 C4 121.4(3) . . ?
C11 C10 H10 119.3 . . ?
C10 C11 H11 119.7 . . ?
C10 C11 C12 120.5(3) . . ?
C12 C11 H11 119.7 . . ?
C2 C12 C11 117.4(3) . . ?
C2 C12 H12 121.3 . . ?
C11 C12 H12 121.3 . . ?
N0AA C13 C5 178.0(3) . . ?
O3 C14 H14A 109.5 . . ?
O3 C14 H14B 109.5 . . ?
O3 C14 H14C 109.5 . . ?
H14A C14 H14B 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 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
O1 N1 1.227(4) . ?
O2 N1 1.226(4) . ?
O3 C9 1.369(3) . ?
O3 C14 1.432(4) . ?
N0AA C13 1.149(4) . ?
N1 C2 1.479(4) . ?
C2 C3 1.385(4) . ?
C2 C12 1.379(4) . ?
C3 H3 0.9500 . ?
C3 C4 1.399(4) . ?
C4 C5 1.486(4) . ?
C4 C10 1.401(4) . ?
C5 C6 1.359(4) . ?
C5 C13 1.441(4) . ?
C6 H6 0.9500 . ?
C6 C7 1.456(4) . ?
C7 C8 1.400(4) 3_766 ?
C7 C9 1.417(4) . ?
C8 C7 1.400(4) 3_766 ?
C8 H8 0.9500 . ?
C8 C9 1.390(4) . ?
C10 H10 0.9500 . ?
C10 C11 1.391(4) . ?
C11 H11 0.9500 . ?
C11 C12 1.392(5) . ?
C12 H12 0.9500 . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 0.9800 . ?
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
O1 N1 C2 C3 0.5(4) . . . . ?
O1 N1 C2 C12 177.0(3) . . . . ?
O2 N1 C2 C3 -178.9(3) . . . . ?
O2 N1 C2 C12 -2.4(4) . . . . ?
N1 C2 C3 C4 176.5(3) . . . . ?
N1 C2 C12 C11 -176.3(3) . . . . ?
C2 C3 C4 C5 -178.4(3) . . . . ?
C2 C3 C4 C10 -0.5(4) . . . . ?
C3 C2 C12 C11 0.0(5) . . . . ?
C3 C4 C5 C6 -14.8(4) . . . . ?
C3 C4 C5 C13 163.3(3) . . . . ?
C3 C4 C10 C11 0.8(4) . . . . ?
C4 C5 C6 C7 179.3(3) . . . . ?
C4 C10 C11 C12 -0.6(5) . . . . ?
C5 C4 C10 C11 178.6(3) . . . . ?
C5 C6 C7 C8 -1.7(5) . . . 3_766 ?
C5 C6 C7 C9 177.6(3) . . . . ?
C6 C7 C9 O3 0.6(4) . . . . ?
C6 C7 C9 C8 -179.2(3) . . . . ?
C7 C8 C9 O3 -179.9(3) 3_766 . . . ?
C7 C8 C9 C7 -0.2(5) 3_766 . . . ?
C8 C7 C9 O3 179.9(3) 3_766 . . . ?
C8 C7 C9 C8 0.2(5) 3_766 . . . ?
C10 C4 C5 C6 167.5(3) . . . . ?
C10 C4 C5 C13 -14.4(4) . . . . ?
C10 C11 C12 C2 0.2(5) . . . . ?
C12 C2 C3 C4 0.2(4) . . . . ?
C13 C5 C6 C7 1.3(5) . . . . ?
C14 O3 C9 C7 -170.0(3) . . . . ?
C14 O3 C9 C8 9.7(4) . . . . ?
