#------------------------------------------------------------------------------
#$Date: 2025-08-18 23:06:14 +0200 (Mon 18 de Aug de 2025) $
#$Revision: 301780 $
#$URL: svn://www.crystallography.net/cod/cif/1/55/42/1554283.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_1554283
loop_
_publ_author_name
'Yao, Wei'
'Sun, Mingtai'
'Zhang, Yuannian'
'Yang, Hui'
'Liang, Dong'
'Wu, Haixia'
'Ni, Runyan'
'Wong, Ming Wah'
'Huang, Dejian'
_publ_section_title
;
 Photo-induced C--H bond activation of N,N′-dialkylethylenediamine
 upon aza-Michael addition to 1,8-pyrenedione: facile synthesis of
 fluorescent pyrene derivatives
;
_journal_issue                   10
_journal_name_full               'Organic Chemistry Frontiers'
_journal_page_first              1679
_journal_paper_doi               10.1039/C8QO00183A
_journal_volume                  5
_journal_year                    2018
_chemical_formula_sum            'C24 H20 N2 O2'
_chemical_formula_weight         368.42
_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
_audit_creation_method           SHELXL-2014/7
_audit_update_record
;
2016-09-02 deposited with the CCDC.
2018-03-27 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 105.603(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   8.0334(12)
_cell_length_b                   24.561(4)
_cell_length_c                   9.1052(13)
_cell_measurement_reflns_used    2750
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      30.01
_cell_measurement_theta_min      2.47
_cell_volume                     1730.3(5)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_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  0.0367
_diffrn_reflns_av_unetI/netI     0.0376
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       27
_diffrn_reflns_limit_k_min       -32
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            13154
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.281
_diffrn_reflns_theta_min         1.658
_exptl_absorpt_coefficient_mu    0.091
_exptl_absorpt_correction_T_max  0.7460
_exptl_absorpt_correction_T_min  0.6412
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Sadabs, (Sheldrick 2012)'
_exptl_crystal_colour            Yellow
_exptl_crystal_density_diffrn    1.414
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'Not Measured'
_exptl_crystal_description       Rod
_exptl_crystal_F_000             776
_exptl_crystal_size_max          0.600
_exptl_crystal_size_mid          0.210
_exptl_crystal_size_min          0.160
_refine_diff_density_max         0.465
_refine_diff_density_min         -0.331
_refine_diff_density_rms         0.072
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.059
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     253
_refine_ls_number_reflns         4292
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.059
_refine_ls_R_factor_all          0.0655
_refine_ls_R_factor_gt           0.0516
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0819P)²+0.0778P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1345
_refine_ls_wR_factor_ref         0.1443
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3349
_reflns_number_total             4292
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            c8qo00183a2.cif
_cod_data_source_block           G236
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_exptl_absorpt_correction_type' value 'Multi-scan' was
changed to 'multi-scan' in accordance with the
/home/saulius/struct/COD-crude-data/automatic-downloads/DataCite-retrospective/RSC/depositions/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 last updated on
2011-04-26.

data item '_exptl_crystal_density_meas' value 'Not Measured' was
changed to '?' -- the value is perceived as not measured.

Automatic conversion script
Id: cif_fix_values 6909 2019-04-08 15:41:33Z antanas 
;
_cod_original_cell_volume        1730.3(4)
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               1554283
_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_min   0.948
_shelx_estimated_absorpt_t_max   0.986
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
O1 O 0.40695(11) 0.44708(4) 0.90722(10) 0.0193(2) Uani 1 1 d . .
O2 O 0.12316(11) 0.47073(4) 0.12045(10) 0.0201(2) Uani 1 1 d . .
N1 N 0.31899(13) 0.50405(4) 0.68940(11) 0.0147(2) Uani 1 1 d . .
N2 N 0.18691(12) 0.51380(4) 0.36300(11) 0.0146(2) Uani 1 1 d . .
C1 C 0.25380(15) 0.56177(5) 0.45874(14) 0.0151(3) Uani 1 1 d . .
H1 H 0.3798 0.5659 0.4671 0.018 Uiso 1 1 calc R U
C2 C 0.15923(17) 0.61346(5) 0.38804(16) 0.0207(3) Uani 1 1 d . .
H2A H 0.1767 0.6190 0.2855 0.025 Uiso 1 1 calc R U
H2B H 0.0338 0.6090 0.3758 0.025 Uiso 1 1 calc R U
C3 C 0.22354(17) 0.66352(5) 0.48612(16) 0.0232(3) Uani 1 1 d . .
H3A H 0.3452 0.6708 0.4876 0.028 Uiso 1 1 calc R U
H3B H 0.1538 0.6956 0.4406 0.028 Uiso 1 1 calc R U
C4 C 0.21142(17) 0.65571(5) 0.64830(16) 0.0226(3) Uani 1 1 d . .
H4A H 0.0883 0.6543 0.6486 0.027 Uiso 1 1 calc R U
H4B H 0.2657 0.6871 0.7113 0.027 Uiso 1 1 calc R U
C5 C 0.30096(16) 0.60351(5) 0.71724(15) 0.0199(3) Uani 1 1 d . .
H5A H 0.2851 0.5985 0.8205 0.024 Uiso 1 1 calc R U
H5B H 0.4264 0.6066 0.7275 0.024 Uiso 1 1 calc R U
C6 C 0.22946(15) 0.55390(5) 0.61933(14) 0.0149(3) Uani 1 1 d . .
H6 H 0.1033 0.5504 0.6113 0.018 Uiso 1 1 calc R U
C7 C 0.28936(15) 0.48914(5) 0.83544(14) 0.0175(3) Uani 1 1 d . .
H7A H 0.3056 0.5215 0.9027 0.021 Uiso 1 1 calc R U
H7B H 0.1690 0.4762 0.8191 0.021 Uiso 1 1 calc R U
C8 C 0.39430(15) 0.40148(5) 0.81793(14) 0.0168(3) Uani 1 1 d . .
C9 C 0.44010(16) 0.35104(5) 0.88602(16) 0.0215(3) Uani 1 1 d . .
H9 H 0.4814 0.3483 0.9938 0.026 Uiso 1 1 calc R U
C10 C 0.42553(16) 0.30482(5) 0.79682(16) 0.0220(3) Uani 1 1 d . .
H10 H 0.4555 0.2705 0.8446 0.026 Uiso 1 1 calc R U
C11 C 0.36784(16) 0.30753(5) 0.63829(16) 0.0193(3) Uani 1 1 d . .
C12 C 0.32523(15) 0.35925(5) 0.56881(15) 0.0155(3) Uani 1 1 d . .
C13 C 0.33684(15) 0.40673(5) 0.65995(14) 0.0142(3) Uani 1 1 d . .
C14 C 0.29557(14) 0.45918(5) 0.59088(14) 0.0133(3) Uani 1 1 d . .
C15 C 0.24003(14) 0.46391(5) 0.43664(14) 0.0129(3) Uani 1 1 d . .
C16 C 0.22947(14) 0.41647(5) 0.34264(14) 0.0147(3) Uani 1 1 d . .
C17 C 0.27247(15) 0.36445(5) 0.40848(14) 0.0151(3) Uani 1 1 d . .
C18 C 0.26044(16) 0.31766(5) 0.31393(16) 0.0191(3) Uani 1 1 d . .
C19 C 0.30418(17) 0.26595(5) 0.38700(17) 0.0230(3) Uani 1 1 d . .
H19 H 0.2985 0.2343 0.3259 0.028 Uiso 1 1 calc R U
C20 C 0.35316(17) 0.26105(5) 0.53994(16) 0.0231(3) Uani 1 1 d . .
H20 H 0.3787 0.2259 0.5839 0.028 Uiso 1 1 calc R U
C21 C 0.20214(16) 0.32474(5) 0.15612(15) 0.0225(3) Uani 1 1 d . .
H21 H 0.1943 0.2940 0.0913 0.027 Uiso 1 1 calc R U
C22 C 0.15550(16) 0.37541(6) 0.09197(15) 0.0221(3) Uani 1 1 d . .
H22 H 0.1137 0.3791 -0.0155 0.026 Uiso 1 1 calc R U
C23 C 0.16985(15) 0.42079(5) 0.18491(14) 0.0173(3) Uani 1 1 d . .
C24 C 0.21512(16) 0.51420(5) 0.21095(14) 0.0184(3) Uani 1 1 d . .
H24A H 0.1757 0.5494 0.1605 0.022 Uiso 1 1 calc R U
H24B H 0.3402 0.5104 0.2199 0.022 Uiso 1 1 calc R U
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
C8 O1 C7 112.56(9)
C23 O2 C24 112.54(9)
C14 N1 C7 111.06(10)
C14 N1 C6 114.20(9)
C7 N1 C6 114.98(9)
C15 N2 C24 110.66(9)
C15 N2 C1 113.43(9)
C24 N2 C1 115.39(9)
N2 C1 C2 110.65(10)
N2 C1 C6 109.96(9)
C2 C1 C6 109.18(10)
N2 C1 H1 109.0
C2 C1 H1 109.0
C6 C1 H1 109.0
C3 C2 C1 111.76(10)
C3 C2 H2A 109.3
C1 C2 H2A 109.3
C3 C2 H2B 109.3
C1 C2 H2B 109.3
H2A C2 H2B 107.9
C4 C3 C2 111.55(10)
C4 C3 H3A 109.3
C2 C3 H3A 109.3
C4 C3 H3B 109.3
C2 C3 H3B 109.3
H3A C3 H3B 108.0
C3 C4 C5 111.17(10)
C3 C4 H4A 109.4
C5 C4 H4A 109.4
C3 C4 H4B 109.4
C5 C4 H4B 109.4
H4A C4 H4B 108.0
C4 C5 C6 111.70(11)
C4 C5 H5A 109.3
C6 C5 H5A 109.3
C4 C5 H5B 109.3
C6 C5 H5B 109.3
H5A C5 H5B 107.9
N1 C6 C5 110.27(10)
N1 C6 C1 110.09(9)
C5 C6 C1 109.29(10)
N1 C6 H6 109.1
C5 C6 H6 109.1
C1 C6 H6 109.1
O1 C7 N1 110.33(9)
O1 C7 H7A 109.6
N1 C7 H7A 109.6
O1 C7 H7B 109.6
N1 C7 H7B 109.6
H7A C7 H7B 108.1
O1 C8 C9 119.67(11)
O1 C8 C13 119.18(11)
C9 C8 C13 121.15(12)
C10 C9 C8 119.96(12)
C10 C9 H9 120.0
C8 C9 H9 120.0
C9 C10 C11 121.42(12)
C9 C10 H10 119.3
C11 C10 H10 119.3
C10 C11 C12 118.52(12)
C10 C11 C20 123.81(12)
C12 C11 C20 117.65(12)
C17 C12 C11 120.73(11)
C17 C12 C13 118.97(11)
C11 C12 C13 120.30(12)
C8 C13 C12 118.62(11)
C8 C13 C14 120.63(11)
C12 C13 C14 120.72(11)
C15 C14 N1 122.98(11)
C15 C14 C13 120.21(11)
N1 C14 C13 116.79(11)
C14 C15 N2 122.69(11)
C14 C15 C16 119.82(11)
N2 C15 C16 117.47(11)
C23 C16 C17 118.93(11)
C23 C16 C15 120.19(11)
C17 C16 C15 120.82(11)
C12 C17 C16 119.41(11)
C12 C17 C18 120.33(11)
C16 C17 C18 120.26(12)
C21 C18 C17 118.10(12)
C21 C18 C19 124.07(12)
C17 C18 C19 117.80(12)
C20 C19 C18 121.75(12)
C20 C19 H19 119.1
C18 C19 H19 119.1
C19 C20 C11 121.73(12)
C19 C20 H20 119.1
C11 C20 H20 119.1
C22 C21 C18 121.60(12)
C22 C21 H21 119.2
C18 C21 H21 119.2
C21 C22 C23 119.83(12)
C21 C22 H22 120.1
C23 C22 H22 120.1
O2 C23 C22 119.42(12)
O2 C23 C16 119.35(11)
C22 C23 C16 121.23(12)
O2 C24 N2 110.71(10)
O2 C24 H24A 109.5
N2 C24 H24A 109.5
O2 C24 H24B 109.5
N2 C24 H24B 109.5
H24A C24 H24B 108.1
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O1 C8 1.3716(15)
O1 C7 1.4334(14)
O2 C23 1.3679(15)
O2 C24 1.4273(15)
N1 C14 1.4014(15)
N1 C7 1.4591(15)
N1 C6 1.4753(15)
N2 C15 1.4068(14)
N2 C24 1.4618(15)
N2 C1 1.4782(15)
C1 C2 1.5298(16)
C1 C6 1.5387(17)
C1 H1 1.0000
C2 C3 1.5258(18)
C2 H2A 0.9900
C2 H2B 0.9900
C3 C4 1.5180(19)
C3 H3A 0.9900
C3 H3B 0.9900
C4 C5 1.5207(17)
C4 H4A 0.9900
C4 H4B 0.9900
C5 C6 1.5276(16)
C5 H5A 0.9900
C5 H5B 0.9900
C6 H6 1.0000
C7 H7A 0.9900
C7 H7B 0.9900
C8 C9 1.3898(17)
C8 C13 1.3934(17)
C9 C10 1.3823(19)
C9 H9 0.9500
C10 C11 1.3939(19)
C10 H10 0.9500
C11 C12 1.4193(17)
C11 C20 1.4361(18)
C12 C17 1.4122(18)
C12 C13 1.4195(17)
C13 C14 1.4328(16)
C14 C15 1.3594(17)
C15 C16 1.4346(16)
C16 C23 1.3904(18)
C16 C17 1.4142(17)
C17 C18 1.4234(17)
C18 C21 1.3972(19)
C18 C19 1.4330(18)
C19 C20 1.347(2)
C19 H19 0.9500
C20 H20 0.9500
C21 C22 1.3831(18)
C21 H21 0.9500
C22 C23 1.3854(18)
C22 H22 0.9500
C24 H24A 0.9900
C24 H24B 0.9900
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
C15 N2 C1 C2 -166.76(10)
C24 N2 C1 C2 64.08(13)
C15 N2 C1 C6 -46.07(12)
C24 N2 C1 C6 -175.23(9)
N2 C1 C2 C3 178.97(10)
C6 C1 C2 C3 57.82(13)
C1 C2 C3 C4 -54.96(14)
C2 C3 C4 C5 52.97(14)
C3 C4 C5 C6 -55.73(14)
C14 N1 C6 C5 -164.23(10)
C7 N1 C6 C5 65.69(13)
C14 N1 C6 C1 -43.56(13)
C7 N1 C6 C1 -173.64(9)
C4 C5 C6 N1 -179.99(10)
C4 C5 C6 C1 58.87(13)
N2 C1 C6 N1 58.13(12)
C2 C1 C6 N1 179.70(9)
N2 C1 C6 C5 179.39(9)
C2 C1 C6 C5 -59.04(13)
C8 O1 C7 N1 -57.58(12)
C14 N1 C7 O1 59.73(12)
C6 N1 C7 O1 -168.67(9)
C7 O1 C8 C9 -153.61(11)
C7 O1 C8 C13 26.90(15)
O1 C8 C9 C10 179.16(11)
C13 C8 C9 C10 -1.37(19)
C8 C9 C10 C11 1.0(2)
C9 C10 C11 C12 0.59(19)
C9 C10 C11 C20 178.83(11)
C10 C11 C12 C17 177.58(11)
C20 C11 C12 C17 -0.77(18)
C10 C11 C12 C13 -1.77(18)
C20 C11 C12 C13 179.88(11)
O1 C8 C13 C12 179.66(10)
C9 C8 C13 C12 0.18(18)
O1 C8 C13 C14 1.60(17)
C9 C8 C13 C14 -177.87(11)
C17 C12 C13 C8 -177.97(10)
C11 C12 C13 C8 1.39(17)
C17 C12 C13 C14 0.08(17)
C11 C12 C13 C14 179.44(10)
C7 N1 C14 C15 150.11(11)
C6 N1 C14 C15 18.11(16)
C7 N1 C14 C13 -31.22(13)
C6 N1 C14 C13 -163.22(10)
C8 C13 C14 C15 179.83(11)
C12 C13 C14 C15 1.82(18)
C8 C13 C14 N1 1.12(17)
C12 C13 C14 N1 -176.89(10)
N1 C14 C15 N2 -5.66(18)
C13 C14 C15 N2 175.71(9)
N1 C14 C15 C16 176.09(10)
C13 C14 C15 C16 -2.54(17)
C24 N2 C15 C14 152.27(11)
C1 N2 C15 C14 20.75(16)
C24 N2 C15 C16 -29.44(13)
C1 N2 C15 C16 -160.96(10)
C14 C15 C16 C23 178.84(11)
N2 C15 C16 C23 0.50(17)
C14 C15 C16 C17 1.44(17)
N2 C15 C16 C17 -176.90(10)
C11 C12 C17 C16 179.47(10)
C13 C12 C17 C16 -1.17(17)
C11 C12 C17 C18 0.31(18)
C13 C12 C17 C18 179.67(10)
C23 C16 C17 C12 -176.98(11)
C15 C16 C17 C12 0.45(17)
C23 C16 C17 C18 2.18(18)
C15 C16 C17 C18 179.62(10)
C12 C17 C18 C21 177.92(11)
C16 C17 C18 C21 -1.24(18)
C12 C17 C18 C19 -0.30(18)
C16 C17 C18 C19 -179.45(11)
C21 C18 C19 C20 -177.27(12)
C17 C18 C19 C20 0.83(19)
C18 C19 C20 C11 -1.4(2)
C10 C11 C20 C19 -176.95(12)
C12 C11 C20 C19 1.31(19)
C17 C18 C21 C22 -0.58(19)
C19 C18 C21 C22 177.51(11)
C18 C21 C22 C23 1.4(2)
C24 O2 C23 C22 -152.14(11)
C24 O2 C23 C16 28.40(15)
C21 C22 C23 O2 -179.90(11)
C21 C22 C23 C16 -0.45(19)
C17 C16 C23 O2 178.11(10)
C15 C16 C23 O2 0.66(18)
C17 C16 C23 C22 -1.34(19)
C15 C16 C23 C22 -178.79(10)
C23 O2 C24 N2 -58.33(13)
C15 N2 C24 O2 58.47(12)
C1 N2 C24 O2 -171.03(9)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 168304330
