#------------------------------------------------------------------------------
#$Date: 2017-10-13 14:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201982 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/02/71/4027132.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_4027132
loop_
_publ_author_name
'Jianhong Chen'
'Weimin Liu'
'Jingjin Ma'
'Haitao Xu'
'Jiasheng Wu'
'Xianglin Tang'
'Zhiyuan Fan'
'Pengfei Wang'
_publ_section_title
;
 Synthesis and Properties of Fluorescence Dyes: Tetracyclic
 Pyrazolo[3,4-b]Pyridine-Based Coumarin Chromophores with Intramolecular
 Charge Transfer Character
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              3475
_journal_page_last               3482
_journal_paper_doi               10.1021/jo3002722
_journal_volume                  77
_journal_year                    2012
_chemical_formula_moiety         'C30 H26 N4 O2'
_chemical_formula_sum            'C30 H26 N4 O2'
_chemical_formula_weight         474.55
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                103.417(8)
_cell_angle_beta                 93.162(6)
_cell_angle_gamma                90.024(5)
_cell_formula_units_Z            2
_cell_length_a                   10.157(3)
_cell_length_b                   10.670(3)
_cell_length_c                   11.257(3)
_cell_measurement_reflns_used    429
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      27.48
_cell_measurement_theta_min      2.17
_cell_volume                     1184.8(6)
_computing_cell_refinement       'CrystalClear (Rigaku Inc., 2007)'
_computing_data_collection       'CrystalClear (Rigaku Inc., 2007)'
_computing_data_reduction        'CrystalClear (Rigaku Inc., 2007)'
_computing_molecular_graphics    'XP in Siemens SHELXTL (Sheldrick, 1994)'
_computing_publication_material  'SHELX97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Saturn724+ CCD'
_diffrn_measurement_method       'ω scans at fixed χ = 45°'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0552
_diffrn_reflns_av_sigmaI/netI    0.0544
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            13324
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         2.37
_exptl_absorpt_coefficient_mu    0.085
_exptl_absorpt_correction_T_max  0.9958
_exptl_absorpt_correction_T_min  0.9832
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'CrystalClear (Rigaku Inc., 2007)'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.330
_exptl_crystal_description       needle
_exptl_crystal_F_000             500
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.245
_refine_diff_density_min         -0.188
_refine_diff_density_rms         0.041
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.211
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     328
_refine_ls_number_reflns         4166
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.211
_refine_ls_R_factor_all          0.0947
_refine_ls_R_factor_gt           0.0756
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0373P)²+0.7448P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1392
_refine_ls_wR_factor_ref         0.1475
_reflns_number_gt                3469
_reflns_number_total             4166
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo3002722_si_008.cif
_cod_data_source_block           sa850
_cod_database_code               4027132
loop_
_symmetry_equiv_pos_as_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
O1 O 0.14197(18) 0.43255(19) 0.06715(17) 0.0372(5) Uani 1 1 d .
O2 O 0.0702(2) 0.5794(2) 0.21751(19) 0.0499(6) Uani 1 1 d .
N1 N 0.2630(2) 0.1713(2) -0.3112(2) 0.0352(6) Uani 1 1 d .
N2 N 0.4432(2) 0.6327(2) 0.4063(2) 0.0310(6) Uani 1 1 d .
N3 N 0.6623(2) 0.5487(2) 0.4001(2) 0.0280(5) Uani 1 1 d .
N4 N 0.7322(2) 0.4542(2) 0.32576(19) 0.0289(5) Uani 1 1 d .
C1 C 0.4122(3) -0.0191(3) -0.3442(3) 0.0475(8) Uani 1 1 d .
H1A H 0.4686 -0.0691 -0.4054 0.071 Uiso 1 1 calc R
H1B H 0.3378 -0.0730 -0.3333 0.071 Uiso 1 1 calc R
H1C H 0.4634 0.0097 -0.2662 0.071 Uiso 1 1 calc R
C2 C 0.3608(3) 0.0972(3) -0.3873(3) 0.0371(7) Uani 1 1 d .
H2A H 0.4363 0.1548 -0.3904 0.045 Uiso 1 1 calc R
H2B H 0.3213 0.0676 -0.4716 0.045 Uiso 1 1 calc R
C3 C 0.0594(3) 0.0398(3) -0.3139(3) 0.0584(10) Uani 1 1 d .
H3A H -0.0351 0.0368 -0.3372 0.088 Uiso 1 1 calc R
H3B H 0.0721 0.0525 -0.2250 0.088 Uiso 1 1 calc R
H3C H 0.0995 -0.0415 -0.3540 0.088 Uiso 1 1 calc R
C4 C 0.1242(3) 0.1509(3) -0.3537(3) 0.0405(8) Uani 1 1 d .
H4A H 0.1175 0.1336 -0.4442 0.049 Uiso 1 1 calc R
H4B H 0.0754 0.2308 -0.3219 0.049 Uiso 1 1 calc R
C5 C 0.2984(3) 0.2413(3) -0.1959(2) 0.0290(6) Uani 1 1 d .
C6 C 0.2046(3) 0.3037(3) -0.1163(3) 0.0332(7) Uani 1 1 d .
H6A H 0.1138 0.2983 -0.1426 0.040 Uiso 1 1 calc R
C7 C 0.2430(3) 0.3725(3) -0.0005(2) 0.0298(6) Uani 1 1 d .
C8 C 0.3736(3) 0.3839(3) 0.0476(2) 0.0290(6) Uani 1 1 d .
C9 C 0.4673(3) 0.3283(3) -0.0361(2) 0.0291(6) Uani 1 1 d .
H9A H 0.5582 0.3391 -0.0108 0.035 Uiso 1 1 calc R
C10 C 0.4330(3) 0.2596(3) -0.1520(2) 0.0305(6) Uani 1 1 d .
H10A H 0.5003 0.2233 -0.2043 0.037 Uiso 1 1 calc R
C11 C 0.1654(3) 0.5216(3) 0.1752(3) 0.0351(7) Uani 1 1 d .
C12 C 0.3003(3) 0.5335(3) 0.2322(2) 0.0288(6) Uani 1 1 d .
C13 C 0.4015(3) 0.4561(2) 0.1713(2) 0.0277(6) Uani 1 1 d .
C14 C 0.3251(3) 0.6203(3) 0.3476(3) 0.0327(7) Uani 1 1 d .
C15 C 0.5366(3) 0.5524(2) 0.3519(2) 0.0264(6) Uani 1 1 d .
C16 C 0.5248(3) 0.4612(2) 0.2404(2) 0.0262(6) Uani 1 1 d .
C17 C 0.2231(3) 0.7083(3) 0.4131(3) 0.0472(9) Uani 1 1 d .
H17A H 0.2624 0.7589 0.4909 0.071 Uiso 1 1 calc R
H17B H 0.1489 0.6568 0.4288 0.071 Uiso 1 1 calc R
H17C H 0.1916 0.7665 0.3622 0.071 Uiso 1 1 calc R
C18 C 0.6521(3) 0.4002(3) 0.2308(2) 0.0271(6) Uani 1 1 d .
C19 C 0.7052(3) 0.2889(3) 0.1436(2) 0.0292(6) Uani 1 1 d .
C20 C 0.8262(3) 0.3006(3) 0.0952(3) 0.0385(7) Uani 1 1 d .
H20A H 0.8728 0.3806 0.1161 0.046 Uiso 1 1 calc R
C21 C 0.8788(3) 0.1955(3) 0.0161(3) 0.0509(9) Uani 1 1 d .
H21A H 0.9610 0.2040 -0.0178 0.061 Uiso 1 1 calc R
C22 C 0.8120(3) 0.0787(3) -0.0132(3) 0.0555(10) Uani 1 1 d .
H22A H 0.8487 0.0068 -0.0670 0.067 Uiso 1 1 calc R
C23 C 0.6923(3) 0.0661(3) 0.0353(3) 0.0476(8) Uani 1 1 d .
H23A H 0.6467 -0.0145 0.0155 0.057 Uiso 1 1 calc R
C24 C 0.6386(3) 0.1711(3) 0.1128(3) 0.0359(7) Uani 1 1 d .
H24A H 0.5555 0.1626 0.1451 0.043 Uiso 1 1 calc R
C25 C 0.7287(3) 0.6234(2) 0.5087(2) 0.0274(6) Uani 1 1 d .
C26 C 0.6598(3) 0.7051(3) 0.5985(2) 0.0294(6) Uani 1 1 d .
H26A H 0.5669 0.7129 0.5887 0.035 Uiso 1 1 calc R
C27 C 0.7291(3) 0.7751(3) 0.7025(3) 0.0354(7) Uani 1 1 d .
H27A H 0.6833 0.8324 0.7635 0.042 Uiso 1 1 calc R
C28 C 0.8639(3) 0.7625(3) 0.7186(3) 0.0371(7) Uani 1 1 d .
H28A H 0.9102 0.8098 0.7908 0.044 Uiso 1 1 calc R
C29 C 0.9307(3) 0.6810(3) 0.6294(3) 0.0374(7) Uani 1 1 d .
H29A H 1.0234 0.6719 0.6405 0.045 Uiso 1 1 calc R
C30 C 0.8643(3) 0.6120(3) 0.5235(3) 0.0343(7) Uani 1 1 d .
H30A H 0.9114 0.5574 0.4616 0.041 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
C11 O1 C7 122.1(2)
C5 N1 C2 120.5(2)
C5 N1 C4 121.0(2)
C2 N1 C4 117.7(2)
C14 N2 C15 115.5(2)
C15 N3 N4 110.2(2)
C15 N3 C25 131.8(2)
N4 N3 C25 118.1(2)
C18 N4 N3 107.2(2)
C2 C1 H1A 109.5
C2 C1 H1B 109.5
H1A C1 H1B 109.5
C2 C1 H1C 109.5
H1A C1 H1C 109.5
H1B C1 H1C 109.5
N1 C2 C1 114.8(2)
N1 C2 H2A 108.6
C1 C2 H2A 108.6
N1 C2 H2B 108.6
C1 C2 H2B 108.6
H2A C2 H2B 107.5
C4 C3 H3A 109.5
C4 C3 H3B 109.5
H3A C3 H3B 109.5
C4 C3 H3C 109.5
H3A C3 H3C 109.5
H3B C3 H3C 109.5
N1 C4 C3 113.2(3)
N1 C4 H4A 108.9
C3 C4 H4A 108.9
N1 C4 H4B 108.9
C3 C4 H4B 108.9
H4A C4 H4B 107.7
N1 C5 C6 121.8(2)
N1 C5 C10 121.8(2)
C6 C5 C10 116.3(2)
C7 C6 C5 120.5(3)
C7 C6 H6A 119.7
C5 C6 H6A 119.7
C6 C7 O1 114.8(2)
C6 C7 C8 124.0(3)
O1 C7 C8 121.1(2)
C7 C8 C9 114.7(2)
C7 C8 C13 119.1(2)
C9 C8 C13 126.2(2)
C10 C9 C8 122.8(3)
C10 C9 H9A 118.6
C8 C9 H9A 118.6
C9 C10 C5 121.3(3)
C9 C10 H10A 119.3
C5 C10 H10A 119.3
O2 C11 O1 115.6(2)
O2 C11 C12 126.2(3)
O1 C11 C12 118.1(2)
C14 C12 C13 121.9(2)
C14 C12 C11 119.0(2)
C13 C12 C11 119.2(2)
C12 C13 C16 115.3(2)
C12 C13 C8 118.6(2)
C16 C13 C8 126.1(2)
N2 C14 C12 122.2(3)
N2 C14 C17 113.9(2)
C12 C14 C17 123.9(2)
N2 C15 N3 123.9(2)
N2 C15 C16 128.0(2)
N3 C15 C16 108.1(2)
C15 C16 C13 116.6(2)
C15 C16 C18 104.0(2)
C13 C16 C18 139.4(2)
C14 C17 H17A 109.5
C14 C17 H17B 109.5
H17A C17 H17B 109.5
C14 C17 H17C 109.5
H17A C17 H17C 109.5
H17B C17 H17C 109.5
N4 C18 C16 110.4(2)
N4 C18 C19 115.9(2)
C16 C18 C19 133.6(2)
C20 C19 C24 119.3(3)
C20 C19 C18 119.6(3)
C24 C19 C18 121.1(2)
C21 C20 C19 120.0(3)
C21 C20 H20A 120.0
C19 C20 H20A 120.0
C22 C21 C20 120.2(3)
C22 C21 H21A 119.9
C20 C21 H21A 119.9
C23 C22 C21 120.1(3)
C23 C22 H22A 119.9
C21 C22 H22A 119.9
C22 C23 C24 119.9(3)
C22 C23 H23A 120.1
C24 C23 H23A 120.1
C23 C24 C19 120.5(3)
C23 C24 H24A 119.7
C19 C24 H24A 119.7
C30 C25 C26 120.4(2)
C30 C25 N3 118.3(2)
C26 C25 N3 121.3(2)
C27 C26 C25 118.9(3)
C27 C26 H26A 120.5
C25 C26 H26A 120.5
C28 C27 C26 120.9(3)
C28 C27 H27A 119.5
C26 C27 H27A 119.5
C29 C28 C27 119.6(3)
C29 C28 H28A 120.2
C27 C28 H28A 120.2
C28 C29 C30 120.7(3)
C28 C29 H29A 119.6
C30 C29 H29A 119.6
C29 C30 C25 119.5(3)
C29 C30 H30A 120.2
C25 C30 H30A 120.2
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O1 C11 1.368(3)
O1 C7 1.380(3)
O2 C11 1.207(3)
N1 C5 1.368(3)
N1 C2 1.458(3)
N1 C4 1.463(4)
N2 C14 1.329(3)
N2 C15 1.353(3)
N3 C15 1.364(3)
N3 N4 1.377(3)
N3 C25 1.428(3)
N4 C18 1.324(3)
C1 C2 1.516(4)
C1 H1A 0.9800
C1 H1B 0.9800
C1 H1C 0.9800
C2 H2A 0.9900
C2 H2B 0.9900
C3 C4 1.523(5)
C3 H3A 0.9800
C3 H3B 0.9800
C3 H3C 0.9800
C4 H4A 0.9900
C4 H4B 0.9900
C5 C6 1.405(4)
C5 C10 1.426(4)
C6 C7 1.374(4)
C6 H6A 0.9500
C7 C8 1.399(4)
C8 C9 1.409(4)
C8 C13 1.439(4)
C9 C10 1.366(4)
C9 H9A 0.9500
C10 H10A 0.9500
C11 C12 1.473(4)
C12 C14 1.419(4)
C12 C13 1.423(4)
C13 C16 1.431(4)
C14 C17 1.504(4)
C15 C16 1.398(4)
C16 C18 1.446(4)
C17 H17A 0.9800
C17 H17B 0.9800
C17 H17C 0.9800
C18 C19 1.478(4)
C19 C20 1.388(4)
C19 C24 1.389(4)
C20 C21 1.387(4)
C20 H20A 0.9500
C21 C22 1.381(5)
C21 H21A 0.9500
C22 C23 1.379(5)
C22 H22A 0.9500
C23 C24 1.383(4)
C23 H23A 0.9500
C24 H24A 0.9500
C25 C30 1.388(4)
C25 C26 1.393(4)
C26 C27 1.388(4)
C26 H26A 0.9500
C27 C28 1.381(4)
C27 H27A 0.9500
C28 C29 1.378(4)
C28 H28A 0.9500
C29 C30 1.386(4)
C29 H29A 0.9500
C30 H30A 0.9500
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 N3 N4 C18 0.9(3)
C25 N3 N4 C18 -178.8(2)
C5 N1 C2 C1 69.3(3)
C4 N1 C2 C1 -100.6(3)
C5 N1 C4 C3 -82.9(3)
C2 N1 C4 C3 86.9(3)
C2 N1 C5 C6 -173.8(2)
C4 N1 C5 C6 -4.3(4)
C2 N1 C5 C10 9.0(4)
C4 N1 C5 C10 178.5(3)
N1 C5 C6 C7 179.5(3)
C10 C5 C6 C7 -3.2(4)
C5 C6 C7 O1 178.0(2)
C5 C6 C7 C8 -1.4(4)
C11 O1 C7 C6 -168.8(3)
C11 O1 C7 C8 10.5(4)
C6 C7 C8 C9 5.4(4)
O1 C7 C8 C9 -173.9(2)
C6 C7 C8 C13 -178.5(3)
O1 C7 C8 C13 2.1(4)
C7 C8 C9 C10 -5.1(4)
C13 C8 C9 C10 179.2(3)
C8 C9 C10 C5 0.8(4)
N1 C5 C10 C9 -179.2(3)
C6 C5 C10 C9 3.5(4)
C7 O1 C11 O2 170.7(3)
C7 O1 C11 C12 -12.6(4)
O2 C11 C12 C14 -0.2(5)
O1 C11 C12 C14 -176.6(2)
O2 C11 C12 C13 178.7(3)
O1 C11 C12 C13 2.3(4)
C14 C12 C13 C16 6.9(4)
C11 C12 C13 C16 -172.0(2)
C14 C12 C13 C8 -171.5(3)
C11 C12 C13 C8 9.6(4)
C7 C8 C13 C12 -11.9(4)
C9 C8 C13 C12 163.7(3)
C7 C8 C13 C16 169.9(3)
C9 C8 C13 C16 -14.6(4)
C15 N2 C14 C12 -3.3(4)
C15 N2 C14 C17 178.1(3)
C13 C12 C14 N2 -1.3(4)
C11 C12 C14 N2 177.6(3)
C13 C12 C14 C17 177.2(3)
C11 C12 C14 C17 -3.9(4)
C14 N2 C15 N3 -178.2(3)
C14 N2 C15 C16 2.0(4)
N4 N3 C15 N2 177.8(2)
C25 N3 C15 N2 -2.4(5)
N4 N3 C15 C16 -2.3(3)
C25 N3 C15 C16 177.4(3)
N2 C15 C16 C13 3.8(4)
N3 C15 C16 C13 -176.0(2)
N2 C15 C16 C18 -177.5(3)
N3 C15 C16 C18 2.7(3)
C12 C13 C16 C15 -7.8(4)
C8 C13 C16 C15 170.5(2)
C12 C13 C16 C18 174.2(3)
C8 C13 C16 C18 -7.5(5)
N3 N4 C18 C16 0.8(3)
N3 N4 C18 C19 -175.7(2)
C15 C16 C18 N4 -2.2(3)
C13 C16 C18 N4 176.0(3)
C15 C16 C18 C19 173.5(3)
C13 C16 C18 C19 -8.4(6)
N4 C18 C19 C20 -52.4(4)
C16 C18 C19 C20 132.2(3)
N4 C18 C19 C24 125.2(3)
C16 C18 C19 C24 -50.2(4)
C24 C19 C20 C21 0.4(4)
C18 C19 C20 C21 178.0(3)
C19 C20 C21 C22 -0.8(5)
C20 C21 C22 C23 0.4(5)
C21 C22 C23 C24 0.5(5)
C22 C23 C24 C19 -0.9(5)
C20 C19 C24 C23 0.5(4)
C18 C19 C24 C23 -177.1(3)
C15 N3 C25 C30 -169.2(3)
N4 N3 C25 C30 10.5(4)
C15 N3 C25 C26 11.3(4)
N4 N3 C25 C26 -169.0(2)
C30 C25 C26 C27 0.2(4)
N3 C25 C26 C27 179.7(2)
C25 C26 C27 C28 -1.3(4)
C26 C27 C28 C29 1.0(5)
C27 C28 C29 C30 0.3(5)
C28 C29 C30 C25 -1.4(5)
C26 C25 C30 C29 1.1(4)
N3 C25 C30 C29 -178.4(3)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 30659485
