#------------------------------------------------------------------------------
#$Date: 2016-03-22 11:36:53 +0200 (Tue, 22 Mar 2016) $
#$Revision: 178907 $
#$URL: svn://www.crystallography.net/cod/cif/4/11/36/4113607.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_4113607
loop_
_publ_author_name
'Christoph J. Fahrni'
'Liuchun Yang'
'Donald G. VanDerveer'
_publ_contact_author             'Christoph J. Fahrni'
_publ_contact_author_email       fahrni@chemistry.gatech.edu
_publ_section_title
;
 Tuning the Photoinduced Electron-Transfer Thermodynamics in
 1,3,5-Triaryl-2-pyrazoline Fluorophores: X-ray Structures, Photophysical
 Characterization, Computational Analysis, and in Vivo Evaluation
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              3799
_journal_page_last               3812
_journal_paper_doi               10.1021/ja028266o
_journal_volume                  125
_journal_year                    2003
_chemical_formula_sum            'C29 H30 N4 O2'
_chemical_formula_weight         466.57
_chemical_melting_point          362(1)
_chemical_name_systematic
; 
4-[1-(4-Cyano-phenyl)-5-(4-diethylamino-phenyl)-4,5-dihydro-
1H-pyrazol-3-yl]-benzoic acid ethyl ester 
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 94.776(4)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   6.2834(12)
_cell_length_b                   12.271(2)
_cell_length_c                   32.551(6)
_cell_measurement_reflns_used    916
_cell_measurement_temperature    193(2)
_cell_measurement_theta_max      28.51
_cell_measurement_theta_min      2.51
_cell_volume                     2501.1(8)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      193(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker 1K CCD'
_diffrn_measurement_method       'omega scan'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'normal-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0390
_diffrn_reflns_av_sigmaI/netI    0.0439
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       38
_diffrn_reflns_limit_l_min       -38
_diffrn_reflns_number            12488
_diffrn_reflns_theta_full        25.10
_diffrn_reflns_theta_max         25.10
_diffrn_reflns_theta_min         1.77
_exptl_absorpt_coefficient_mu    0.079
_exptl_absorpt_correction_T_max  0.9941
_exptl_absorpt_correction_T_min  0.9095
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Blessing, Acta Cryst. (1995) A51 33-38'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.239
_exptl_crystal_description       needle
_exptl_crystal_F_000             992
_exptl_crystal_size_max          1.22
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.170
_refine_diff_density_min         -0.391
_refine_diff_density_rms         0.036
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.033
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     343
_refine_ls_number_reflns         4458
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.033
_refine_ls_R_factor_all          0.0677
_refine_ls_R_factor_gt           0.0453
_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)+(0.0407P)²+0.9327P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1021
_refine_ls_wR_factor_ref         0.1137
_reflns_number_gt                3316
_reflns_number_total             4458
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja028266osi20021210_012116_5.cif
_cod_data_source_block           2c
_cod_original_cell_volume        2501.2(8)
_cod_database_code               4113607
loop_
_symmetry_equiv_pos_as_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
N1 N 1.0148(2) -0.76302(13) -0.34345(5) 0.0325(4) Uani 1 1 d .
N2 N 0.8472(2) -0.71625(13) -0.32538(5) 0.0317(4) Uani 1 1 d .
C3 C 0.7747(3) -0.78526(15) -0.30001(5) 0.0291(4) Uani 1 1 d .
C4 C 0.8954(3) -0.89120(16) -0.29753(6) 0.0311(4) Uani 1 1 d .
H4A H 0.8020 -0.9518 -0.3041 0.038(4) Uiso 1 1 calc R
H4B H 0.9666 -0.9018 -0.2706 0.038(4) Uiso 1 1 calc R
C5 C 1.0577(3) -0.87714(15) -0.33019(6) 0.0291(4) Uani 1 1 d .
H5 H 1.2062 -0.8831 -0.3167 0.026(5) Uiso 1 1 calc R
C6 C 1.1364(3) -0.70035(15) -0.36767(5) 0.0302(4) Uani 1 1 d .
C7 C 1.3239(3) -0.74179(16) -0.38192(6) 0.0333(4) Uani 1 1 d .
H7 H 1.3660 -0.8155 -0.3756 0.033(5) Uiso 1 1 calc R
C8 C 1.4489(3) -0.67773(17) -0.40503(6) 0.0364(5) Uani 1 1 d .
H8 H 1.5782 -0.7069 -0.4144 0.035(5) Uiso 1 1 calc R
C9 C 1.3892(3) -0.57115(17) -0.41495(6) 0.0397(5) Uani 1 1 d .
C10 C 1.2004(4) -0.53098(18) -0.40136(7) 0.0495(6) Uani 1 1 d .
H10 H 1.1566 -0.4579 -0.4084 0.061(7) Uiso 1 1 calc R
C11 C 1.0754(3) -0.59373(17) -0.37805(7) 0.0427(5) Uani 1 1 d .
H11 H 0.9460 -0.5643 -0.3689 0.050(6) Uiso 1 1 calc R
C12 C 0.5925(3) -0.75729(15) -0.27690(5) 0.0298(4) Uani 1 1 d .
C13 C 0.4926(3) -0.65561(16) -0.28213(6) 0.0351(5) Uani 1 1 d .
H13 H 0.5454 -0.6034 -0.3008 0.035(5) Uiso 1 1 calc R
C14 C 0.3193(3) -0.62996(16) -0.26076(6) 0.0352(5) Uani 1 1 d .
H14 H 0.2523 -0.5600 -0.2647 0.059(7) Uiso 1 1 calc R
C15 C 0.2402(3) -0.70413(15) -0.23353(6) 0.0299(4) Uani 1 1 d .
C16 C 0.3393(3) -0.80501(16) -0.22788(6) 0.0320(4) Uani 1 1 d .
H16 H 0.2874 -0.8565 -0.2089 0.038(6) Uiso 1 1 calc R
C17 C 0.5132(3) -0.83154(16) -0.24965(6) 0.0321(4) Uani 1 1 d .
H17 H 0.5793 -0.9018 -0.2459 0.046(6) Uiso 1 1 calc R
C18 C 1.0286(3) -0.95644(15) -0.36570(5) 0.0265(4) Uani 1 1 d .
C19 C 1.1862(3) -1.03073(15) -0.37390(6) 0.0316(4) Uani 1 1 d .
H19 H 1.3194 -1.0297 -0.3571 0.042(6) Uiso 1 1 calc R
C20 C 1.1577(3) -1.10609(16) -0.40541(6) 0.0329(4) Uani 1 1 d .
H20 H 1.2713 -1.1558 -0.4100 0.037(5) Uiso 1 1 calc R
C21 C 0.9661(3) -1.11169(15) -0.43088(5) 0.0296(4) Uani 1 1 d .
C22 C 0.8076(3) -1.03500(16) -0.42267(6) 0.0321(4) Uani 1 1 d .
H22 H 0.6746 -1.0348 -0.4395 0.043(6) Uiso 1 1 calc R
C23 C 0.8396(3) -0.96052(15) -0.39113(6) 0.0312(4) Uani 1 1 d .
H23 H 0.7278 -0.9097 -0.3865 0.035(5) Uiso 1 1 calc R
N24 N 0.9308(3) -1.18695(14) -0.46215(5) 0.0377(4) Uani 1 1 d .
C25 C 1.0823(4) -1.2714(2) -0.47058(7) 0.0553(7) Uani 1 1 d .
H25A H 0.2050 -1.2806 -0.4459 0.061(7) Uiso 1 1 d .
H25B H 1.0030 -1.3595 -0.4719 0.026(9) Uiso 0.50 1 d P
H25C H 1.1870 -1.2194 -0.4856 0.063(15) Uiso 0.50 1 d P
C26 C 1.0806(19) -1.3319(10) -0.5057(3) 0.050(3) Uiso 0.20 1 d P
H26A H 1.0285 -1.2882 -0.5289 0.032(15) Uiso 0.20 1 calc PR
H26B H 0.9892 -1.3940 -0.5036 0.032(15) Uiso 0.20 1 calc PR
H26C H 1.2230 -1.3562 -0.5095 0.032(15) Uiso 0.20 1 calc PR
C26' C 1.1725(5) -1.2654(3) -0.51115(10) 0.0629(9) Uiso 0.80 1 d P
H26D H 1.0604 -1.2752 -0.5327 0.086(7) Uiso 0.80 1 calc PR
H26E H 1.2777 -1.3215 -0.5129 0.086(7) Uiso 0.80 1 calc PR
H26F H 1.2380 -1.1954 -0.5141 0.086(7) Uiso 0.80 1 calc PR
C27 C 0.7315(3) -1.18659(17) -0.48846(6) 0.0385(5) Uani 1 1 d .
H27A H 0.6150 -1.1767 -0.4715 0.038(4) Uiso 1 1 calc R
H27B H 0.7137 -1.2564 -0.5016 0.038(4) Uiso 1 1 calc R
C28 C 0.7202(4) -1.09903(18) -0.52127(6) 0.0453(5) Uani 1 1 d .
H28A H 0.8324 -1.1101 -0.5391 0.059(4) Uiso 1 1 calc R
H28B H 0.7366 -1.0288 -0.5084 0.059(4) Uiso 1 1 calc R
H28C H 0.5845 -1.1026 -0.5371 0.059(4) Uiso 1 1 calc R
C29 C 1.5218(4) -0.50368(18) -0.43832(7) 0.0479(6) Uani 1 1 d .
N30 N 1.6291(4) -0.44899(18) -0.45626(7) 0.0677(6) Uani 1 1 d .
C31 C 0.0536(3) -0.67105(16) -0.21126(6) 0.0320(4) Uani 1 1 d .
O32 O -0.0295(2) -0.58239(12) -0.21442(5) 0.0444(4) Uani 1 1 d .
O33 O -0.0129(2) -0.74960(11) -0.18695(4) 0.0376(3) Uani 1 1 d .
C34 C -0.1908(3) -0.72128(18) -0.16313(6) 0.0414(5) Uani 1 1 d .
H34A H -0.3118 -0.6990 -0.1811 0.046(4) Uiso 1 1 calc R
H34B H -0.1517 -0.6624 -0.1446 0.046(4) Uiso 1 1 calc R
C35 C -0.2434(4) -0.8202(2) -0.13965(8) 0.0685(8) Uani 1 1 d .
H35A H -0.1229 -0.8400 -0.1211 0.082(5) Uiso 1 1 calc R
H35B H -0.2775 -0.8790 -0.1585 0.082(5) Uiso 1 1 calc R
H35C H -0.3638 -0.8053 -0.1242 0.082(5) 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
N2 N1 C6 119.56(15)
N2 N1 C5 113.38(14)
C6 N1 C5 126.71(15)
C3 N2 N1 108.87(15)
N2 C3 C12 120.51(17)
N2 C3 C4 113.45(16)
C12 C3 C4 126.04(16)
C3 C4 C5 103.04(15)
N1 C5 C18 112.21(15)
N1 C5 C4 101.06(14)
C18 C5 C4 114.23(15)
N1 C6 C11 120.49(17)
N1 C6 C7 120.66(17)
C11 C6 C7 118.85(18)
C8 C7 C6 120.54(19)
C7 C8 C9 120.53(19)
C10 C9 C8 118.70(18)
C10 C9 C29 120.8(2)
C8 C9 C29 120.5(2)
C11 C10 C9 121.3(2)
C10 C11 C6 120.1(2)
C17 C12 C13 118.67(17)
C17 C12 C3 120.75(17)
C13 C12 C3 120.58(17)
C14 C13 C12 120.51(18)
C13 C14 C15 120.82(19)
C14 C15 C16 119.11(17)
C14 C15 C31 118.09(17)
C16 C15 C31 122.79(17)
C17 C16 C15 120.23(18)
C16 C17 C12 120.66(18)
C19 C18 C23 116.73(17)
C19 C18 C5 121.81(16)
C23 C18 C5 121.44(16)
C20 C19 C18 122.10(17)
C19 C20 C21 121.50(17)
N24 C21 C20 123.05(17)
N24 C21 C22 120.92(17)
C20 C21 C22 116.03(17)
C23 C22 C21 121.49(17)
C22 C23 C18 122.14(17)
C21 N24 C25 123.47(17)
C21 N24 C27 120.62(16)
C25 N24 C27 115.89(17)
C26 C25 N24 126.1(5)
C26 C25 C26' 41.9(5)
N24 C25 C26' 116.0(2)
N24 C27 C28 113.87(17)
N30 C29 C9 178.7(3)
O32 C31 O33 123.12(17)
O32 C31 C15 123.90(18)
O33 C31 C15 112.98(16)
C31 O33 C34 115.82(15)
O33 C34 C35 107.03(18)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
N1 N2 1.374(2)
N1 C6 1.377(2)
N1 C5 1.483(2)
N2 C3 1.292(2)
C3 C12 1.462(2)
C3 C4 1.504(3)
C4 C5 1.543(2)
C5 C18 1.511(2)
C6 C11 1.397(3)
C6 C7 1.398(3)
C7 C8 1.378(3)
C8 C9 1.391(3)
C9 C10 1.390(3)
C9 C29 1.437(3)
C10 C11 1.373(3)
C12 C17 1.392(3)
C12 C13 1.401(3)
C13 C14 1.376(3)
C14 C15 1.391(3)
C15 C16 1.391(3)
C15 C31 1.485(3)
C16 C17 1.390(3)
C18 C19 1.388(2)
C18 C23 1.391(2)
C19 C20 1.382(3)
C20 C21 1.405(3)
C21 N24 1.379(2)
C21 C22 1.412(3)
C22 C23 1.377(3)
N24 C25 1.449(3)
N24 C27 1.457(3)
C25 C26 1.363(11)
C25 C26' 1.482(4)
C27 C28 1.512(3)
C29 N30 1.145(3)
C31 O32 1.207(2)
C31 O33 1.336(2)
O33 C34 1.454(2)
C34 C35 1.486(3)
