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#$Revision: 301834 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/12/58/4125842.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.
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data_4125842
loop_
_publ_author_name
'Calbo, Joaquín'
'Weston, Claire E.'
'White, Andrew J. P.'
'Rzepa, Henry S.'
'Contreras-García, Julia'
'Fuchter, Matthew J.'
_publ_section_title
;
 Tuning Azoheteroarene Photoswitch Performance through Heteroaryl Design.
;
_journal_issue                   3
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              1261
_journal_page_last               1274
_journal_paper_doi               10.1021/jacs.6b11626
_journal_volume                  139
_journal_year                    2017
_chemical_formula_moiety         'C9 H9 N5'
_chemical_formula_sum            'C9 H9 N5'
_chemical_formula_weight         187.21
_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                 111.348(7)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   9.2667(6)
_cell_length_b                   10.0686(5)
_cell_length_c                   10.9395(7)
_cell_measurement_reflns_used    1211
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      26.5430
_cell_measurement_theta_min      3.1320
_cell_volume                     950.65(11)
_computing_cell_refinement       'CrysAlisPro, Agilent Technologies'
_computing_data_collection       'CrysAlisPro, Agilent Technologies'
_computing_data_reduction        'CrysAlisPro, Agilent Technologies'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'CIFTAB-2014 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXS-2014 (Sheldrick, 2014)'
_diffrn_ambient_temperature      173(2)
_diffrn_detector_area_resol_mean 16.0382
_diffrn_measured_fraction_theta_full 0.987
_diffrn_measured_fraction_theta_max 0.811
_diffrn_measurement_device_type  'Agilent Xcalibur 3 E'
_diffrn_measurement_method       'omega scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0177
_diffrn_reflns_av_unetI/netI     0.0357
_diffrn_reflns_Laue_measured_fraction_full 0.987
_diffrn_reflns_Laue_measured_fraction_max 0.811
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            3265
_diffrn_reflns_point_group_measured_fraction_full 0.987
_diffrn_reflns_point_group_measured_fraction_max 0.811
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.169
_diffrn_reflns_theta_min         2.844
_diffrn_source                   'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.087
_exptl_absorpt_correction_T_max  0.988
_exptl_absorpt_correction_T_min  0.977
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details
; 
CrysAlisPro, Agilent Technologies, 
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET) 
(compiled Aug 13 2014,18:06:01) 
Analytical numeric absorption correction using a multifaceted crystal 
model based on expressions derived by R.C. Clark & J.S. Reid. 
(Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897) 
Empirical absorption correction using spherical harmonics, 
implemented in SCALE3 ABSPACK scaling algorithm. 
;
_exptl_crystal_colour            Orange
_exptl_crystal_density_diffrn    1.308
_exptl_crystal_description       blocks
_exptl_crystal_F_000             392
_exptl_crystal_size_max          0.45
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.17
_refine_diff_density_max         0.189
_refine_diff_density_min         -0.166
_refine_diff_density_rms         0.035
_refine_ls_extinction_coef       0.011(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_goodness_of_fit_ref   1.034
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     129
_refine_ls_number_reflns         1897
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.034
_refine_ls_R_factor_all          0.0559
_refine_ls_R_factor_gt           0.0393
_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)+(0.0432P)²+0.1257P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0932
_refine_ls_wR_factor_ref         0.1033
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1452
_reflns_number_total             1897
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            ja6b11626_si_002.cif
_cod_data_source_block           3tri
_cod_database_code               4125842
_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
N1 N 0.41890(14) 0.17113(12) 0.34938(11) 0.0351(3) Uani 1 1 d . .
N2 N 0.46779(14) 0.23567(12) 0.46553(11) 0.0347(3) Uani 1 1 d . .
C3 C 0.57133(16) 0.31880(14) 0.45227(13) 0.0305(3) Uani 1 1 d . .
N4 N 0.59233(16) 0.31189(14) 0.33646(12) 0.0480(4) Uani 1 1 d . .
C5 C 0.49329(19) 0.21807(18) 0.27542(16) 0.0481(5) Uani 1 1 d . .
H5A H 0.4771 0.1878 0.1892 0.058 Uiso 1 1 calc R U
C6 C 0.30079(19) 0.06904(16) 0.31988(16) 0.0480(4) Uani 1 1 d . .
H6A H 0.3316 0.0019 0.3895 0.072 Uiso 1 1 calc R U
H6B H 0.2886 0.0272 0.2358 0.072 Uiso 1 1 calc R U
H6C H 0.2022 0.1091 0.3144 0.072 Uiso 1 1 calc R U
N7 N 0.64938(13) 0.40051(11) 0.56006(11) 0.0321(3) Uani 1 1 d . .
N8 N 0.75427(14) 0.47031(12) 0.54589(11) 0.0346(3) Uani 1 1 d . .
C9 C 0.83844(16) 0.54698(14) 0.65954(14) 0.0323(4) Uani 1 1 d . .
C10 C 0.80259(19) 0.55358(16) 0.77180(15) 0.0428(4) Uani 1 1 d . .
H10A H 0.7146 0.5081 0.7758 0.051 Uiso 1 1 calc R U
C11 C 0.8959(2) 0.62680(17) 0.87766(17) 0.0501(5) Uani 1 1 d . .
H11A H 0.8717 0.6321 0.9548 0.060 Uiso 1 1 calc R U
C12 C 1.02457(18) 0.69259(16) 0.87214(16) 0.0442(4) Uani 1 1 d . .
H12A H 1.0891 0.7418 0.9458 0.053 Uiso 1 1 calc R U
C13 C 1.05903(18) 0.68684(15) 0.76040(16) 0.0431(4) Uani 1 1 d . .
H13A H 1.1467 0.7328 0.7563 0.052 Uiso 1 1 calc R U
C14 C 0.96589(18) 0.61415(14) 0.65407(16) 0.0383(4) Uani 1 1 d . .
H14A H 0.9895 0.6103 0.5766 0.046 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'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
C5 N1 N2 109.37(12)
C5 N1 C6 129.41(13)
N2 N1 C6 121.22(12)
C3 N2 N1 102.12(11)
N2 C3 N4 115.38(13)
N2 C3 N7 116.88(12)
N4 C3 N7 127.71(13)
C5 N4 C3 101.58(13)
N4 C5 N1 111.55(13)
N8 N7 C3 114.22(11)
N7 N8 C9 113.40(12)
C14 C9 C10 119.97(14)
C14 C9 N8 115.55(13)
C10 C9 N8 124.45(13)
C11 C10 C9 119.37(15)
C10 C11 C12 120.38(16)
C13 C12 C11 120.13(15)
C12 C13 C14 119.76(15)
C13 C14 C9 120.39(14)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
N1 C5 1.3264(19)
N1 N2 1.3502(15)
N1 C6 1.4497(19)
N2 C3 1.3204(18)
C3 N4 1.3517(17)
C3 N7 1.4034(17)
N4 C5 1.317(2)
N7 N8 1.2539(15)
N8 C9 1.4297(18)
C9 C14 1.381(2)
C9 C10 1.386(2)
C10 C11 1.380(2)
C11 C12 1.384(2)
C12 C13 1.372(2)
C13 C14 1.379(2)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 139125225
