#------------------------------------------------------------------------------
#$Date: 2017-03-01 23:07:01 +0200 (Wed, 01 Mar 2017) $
#$Revision: 192603 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/12/55/4125549.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_4125549
loop_
_publ_author_name
'Travieso-Puente, Raquel'
'Budzak, Simon'
'Chen, Juan'
'Stacko, Peter'
'Jastrzebski, Johann T. B. H.'
'Jacquemin, Denis'
'Otten, Edwin'
_publ_section_title
;
 Arylazoindazole Photoswitches: Facile Synthesis and Functionalization via
 SNAr Substitution.
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_paper_doi               10.1021/jacs.6b12585
_journal_year                    2017
_chemical_formula_sum            'C25 H19 F4 N4'
_chemical_formula_weight         451.44
_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'
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2014/7
_cell_angle_alpha                90
_cell_angle_beta                 103.073(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   6.7441(4)
_cell_length_b                   23.0301(13)
_cell_length_c                   14.3273(9)
_cell_measurement_reflns_used    9977
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      74.59
_cell_measurement_theta_min      6.34
_cell_volume                     2167.6(2)
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXT (Sheldrick 2015)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0994
_diffrn_reflns_av_unetI/netI     0.0473
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       28
_diffrn_reflns_limit_k_min       -28
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            24720
_diffrn_reflns_point_group_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         74.722
_diffrn_reflns_theta_min         6.343
_exptl_absorpt_coefficient_mu    0.912
_exptl_absorpt_correction_T_max  0.7538
_exptl_absorpt_correction_T_min  0.6661
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            orange
_exptl_crystal_density_diffrn    1.383
_exptl_crystal_description       needle
_exptl_crystal_F_000             932
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.07
_exptl_crystal_size_min          0.03
_refine_diff_density_max         0.246
_refine_diff_density_min         -0.196
_refine_diff_density_rms         0.043
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.076
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     301
_refine_ls_number_reflns         4404
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.076
_refine_ls_R_factor_all          0.0639
_refine_ls_R_factor_gt           0.0463
_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)+(0.0353P)²+1.1040P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0996
_refine_ls_wR_factor_ref         0.1059
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3725
_reflns_number_total             4404
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            ja6b12585_si_001.cif
_cod_data_source_block           cu_molan416_0m_a
_cod_database_code               4125549
_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.
;
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
F1 F 0.38735(13) 0.81335(4) 0.63996(7) 0.0316(2) Uani 1 1 d . .
F2 F 0.76644(14) 0.82770(5) 0.74167(8) 0.0376(3) Uani 1 1 d . .
F3 F 1.01892(13) 0.73774(5) 0.79423(7) 0.0357(3) Uani 1 1 d . .
F4 F 0.89618(12) 0.62722(4) 0.74908(7) 0.0301(2) Uani 1 1 d . .
N1 N 0.46837(17) 0.61295(6) 0.63276(9) 0.0232(3) Uani 1 1 d . .
N2 N 0.27587(17) 0.62466(6) 0.58351(10) 0.0250(3) Uani 1 1 d . .
N3 N 0.05931(18) 0.70195(6) 0.53872(10) 0.0245(3) Uani 1 1 d . .
N4 N 0.03721(18) 0.75539(6) 0.54543(10) 0.0247(3) Uani 1 1 d . .
C1 C 0.5396(2) 0.55408(7) 0.64280(11) 0.0220(3) Uani 1 1 d . .
C2 C 0.6848(2) 0.53625(7) 0.59293(11) 0.0238(3) Uani 1 1 d . .
C3 C 0.7538(2) 0.47947(8) 0.60571(12) 0.0267(4) Uani 1 1 d . .
H3 H 0.8544 0.4667 0.5734 0.032 Uiso 1 1 calc R U
C4 C 0.6809(2) 0.44064(8) 0.66401(12) 0.0277(4) Uani 1 1 d . .
C5 C 0.5312(2) 0.45967(8) 0.70962(12) 0.0268(4) Uani 1 1 d . .
H5 H 0.4770 0.4331 0.7481 0.032 Uiso 1 1 calc R U
C6 C 0.4587(2) 0.51630(7) 0.70069(11) 0.0245(3) Uani 1 1 d . .
C7 C 0.2520(2) 0.68133(7) 0.58595(11) 0.0223(3) Uani 1 1 d . .
C8 C 0.4344(2) 0.70972(7) 0.63832(10) 0.0204(3) Uani 1 1 d . .
C9 C 0.5026(2) 0.76615(7) 0.66366(11) 0.0240(3) Uani 1 1 d . .
C10 C 0.6983(2) 0.77423(8) 0.71557(12) 0.0269(4) Uani 1 1 d . .
C11 C 0.8294(2) 0.72708(8) 0.74349(11) 0.0264(4) Uani 1 1 d . .
C12 C 0.7679(2) 0.67161(7) 0.72066(11) 0.0232(3) Uani 1 1 d . .
C13 C 0.5684(2) 0.66272(7) 0.66707(11) 0.0214(3) Uani 1 1 d . .
C14 C -0.1604(2) 0.77617(7) 0.49880(11) 0.0241(3) Uani 1 1 d . .
C15 C -0.3178(2) 0.74090(8) 0.44970(11) 0.0243(3) Uani 1 1 d . .
H15 H -0.2971 0.7004 0.4437 0.029 Uiso 1 1 calc R U
C16 C -0.5051(2) 0.76583(8) 0.40977(12) 0.0289(4) Uani 1 1 d . .
H16 H -0.6140 0.7421 0.3770 0.035 Uiso 1 1 calc R U
C17 C -0.5347(2) 0.82473(8) 0.41717(13) 0.0337(4) Uani 1 1 d . .
H17 H -0.6634 0.8413 0.3892 0.040 Uiso 1 1 calc R U
C18 C -0.3779(3) 0.85974(9) 0.46520(16) 0.0416(5) Uani 1 1 d . .
H18 H -0.3983 0.9003 0.4699 0.050 Uiso 1 1 calc R U
C19 C -0.1901(3) 0.83514(8) 0.50660(14) 0.0360(4) Uani 1 1 d . .
H19 H -0.0823 0.8589 0.5402 0.043 Uiso 1 1 calc R U
C20 C 0.7618(2) 0.57634(8) 0.52638(12) 0.0303(4) Uani 1 1 d . .
H20A H 0.8100 0.5535 0.4783 0.045 Uiso 1 1 calc R U
H20B H 0.8742 0.5997 0.5631 0.045 Uiso 1 1 calc R U
H20C H 0.6513 0.6020 0.4944 0.045 Uiso 1 1 calc R U
C21 C 0.7599(3) 0.37940(9) 0.67704(15) 0.0432(5) Uani 1 1 d . .
H21A H 0.6464 0.3527 0.6763 0.065 Uiso 1 1 calc R U
H21B H 0.8589 0.3762 0.7385 0.065 Uiso 1 1 calc R U
H21C H 0.8258 0.3695 0.6248 0.065 Uiso 1 1 calc R U
C22 C 0.2986(2) 0.53552(9) 0.75203(13) 0.0341(4) Uani 1 1 d . .
H22A H 0.1671 0.5385 0.7061 0.051 Uiso 1 1 calc R U
H22B H 0.3359 0.5735 0.7818 0.051 Uiso 1 1 calc R U
H22C H 0.2885 0.5071 0.8016 0.051 Uiso 1 1 calc R U
C23 C 0.8418(3) 0.46672(9) 0.94864(13) 0.0352(4) Uani 1 1 d . .
H23 H 0.7330 0.4438 0.9137 0.042 Uiso 1 1 calc R U
C24 C 0.9215(3) 0.51098(9) 0.90367(13) 0.0354(4) Uani 1 1 d . .
H24 H 0.8680 0.5186 0.8376 0.043 Uiso 1 1 calc R U
C25 C 1.0789(3) 0.54417(9) 0.95485(13) 0.0360(4) Uani 1 1 d . .
H25 H 1.1336 0.5747 0.9239 0.043 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 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0727 0.0534 '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
N2 N1 C13 110.95(13) . .
N2 N1 C1 119.94(12) . .
C13 N1 C1 129.11(12) . .
C7 N2 N1 106.94(12) . .
N4 N3 C7 114.22(13) . .
N3 N4 C14 114.15(13) . .
C6 C1 C2 122.26(15) . .
C6 C1 N1 118.81(13) . .
C2 C1 N1 118.92(14) . .
C3 C2 C1 117.55(15) . .
C3 C2 C20 120.67(14) . .
C1 C2 C20 121.77(15) . .
C2 C3 C4 122.25(15) . .
C2 C3 H3 118.9 . .
C4 C3 H3 118.9 . .
C3 C4 C5 118.23(16) . .
C3 C4 C21 121.02(16) . .
C5 C4 C21 120.75(17) . .
C6 C5 C4 122.03(16) . .
C6 C5 H5 119.0 . .
C4 C5 H5 119.0 . .
C5 C6 C1 117.63(14) . .
C5 C6 C22 120.53(16) . .
C1 C6 C22 121.84(15) . .
N2 C7 N3 115.30(13) . .
N2 C7 C8 111.58(13) . .
N3 C7 C8 133.11(15) . .
C9 C8 C13 119.05(13) . .
C9 C8 C7 138.32(14) . .
C13 C8 C7 102.63(13) . .
F1 C9 C10 117.40(15) . .
F1 C9 C8 123.53(13) . .
C10 C9 C8 119.07(15) . .
F2 C10 C9 120.24(16) . .
F2 C10 C11 118.62(13) . .
C9 C10 C11 121.13(15) . .
F3 C11 C12 120.23(15) . .
F3 C11 C10 118.38(15) . .
C12 C11 C10 121.39(14) . .
F4 C12 C11 120.12(13) . .
F4 C12 C13 121.81(15) . .
C11 C12 C13 118.08(15) . .
N1 C13 C12 130.83(15) . .
N1 C13 C8 107.90(12) . .
C12 C13 C8 121.27(15) . .
C19 C14 C15 120.40(14) . .
C19 C14 N4 115.33(14) . .
C15 C14 N4 124.26(15) . .
C16 C15 C14 119.03(16) . .
C16 C15 H15 120.5 . .
C14 C15 H15 120.5 . .
C17 C16 C15 120.62(16) . .
C17 C16 H16 119.7 . .
C15 C16 H16 119.7 . .
C16 C17 C18 120.28(15) . .
C16 C17 H17 119.9 . .
C18 C17 H17 119.9 . .
C17 C18 C19 119.64(18) . .
C17 C18 H18 120.2 . .
C19 C18 H18 120.2 . .
C14 C19 C18 120.03(17) . .
C14 C19 H19 120.0 . .
C18 C19 H19 120.0 . .
C2 C20 H20A 109.5 . .
C2 C20 H20B 109.5 . .
H20A C20 H20B 109.5 . .
C2 C20 H20C 109.5 . .
H20A C20 H20C 109.5 . .
H20B C20 H20C 109.5 . .
C4 C21 H21A 109.5 . .
C4 C21 H21B 109.5 . .
H21A C21 H21B 109.5 . .
C4 C21 H21C 109.5 . .
H21A C21 H21C 109.5 . .
H21B C21 H21C 109.5 . .
C6 C22 H22A 109.5 . .
C6 C22 H22B 109.5 . .
H22A C22 H22B 109.5 . .
C6 C22 H22C 109.5 . .
H22A C22 H22C 109.5 . .
H22B C22 H22C 109.5 . .
C24 C23 C25 119.75(17) . 3_767
C24 C23 H23 120.1 . .
C25 C23 H23 120.1 3_767 .
C25 C24 C23 119.78(17) . .
C25 C24 H24 120.1 . .
C23 C24 H24 120.1 . .
C24 C25 C23 120.46(18) . 3_767
C24 C25 H25 119.8 . .
C23 C25 H25 119.8 3_767 .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
F1 C9 1.3347(18) .
F2 C10 1.3378(19) .
F3 C11 1.3424(16) .
F4 C12 1.3417(18) .
N1 N2 1.3570(16) .
N1 C13 1.364(2) .
N1 C1 1.435(2) .
N2 C7 1.317(2) .
N3 N4 1.246(2) .
N3 C7 1.4052(18) .
N4 C14 1.4313(18) .
C1 C6 1.395(2) .
C1 C2 1.398(2) .
C2 C3 1.386(2) .
C2 C20 1.502(2) .
C3 C4 1.387(2) .
C3 H3 0.9500 .
C4 C5 1.391(2) .
C4 C21 1.504(3) .
C5 C6 1.389(2) .
C5 H5 0.9500 .
C6 C22 1.504(2) .
C7 C8 1.4440(19) .
C8 C9 1.399(2) .
C8 C13 1.411(2) .
C9 C10 1.373(2) .
C10 C11 1.401(2) .
C11 C12 1.360(2) .
C12 C13 1.4047(19) .
C14 C19 1.381(3) .
C14 C15 1.394(2) .
C15 C16 1.388(2) .
C15 H15 0.9500 .
C16 C17 1.379(3) .
C16 H16 0.9500 .
C17 C18 1.383(3) .
C17 H17 0.9500 .
C18 C19 1.392(2) .
C18 H18 0.9500 .
C19 H19 0.9500 .
C20 H20A 0.9800 .
C20 H20B 0.9800 .
C20 H20C 0.9800 .
C21 H21A 0.9800 .
C21 H21B 0.9800 .
C21 H21C 0.9800 .
C22 H22A 0.9800 .
C22 H22B 0.9800 .
C22 H22C 0.9800 .
C23 C24 1.378(3) .
C23 C25 1.388(3) 3_767
C23 H23 0.9500 .
C24 C25 1.377(3) .
C24 H24 0.9500 .
C25 C23 1.388(3) 3_767
C25 H25 0.9500 .
