#------------------------------------------------------------------------------
#$Date: 2016-03-26 21:41:59 +0100 (Sat 26 de Mar de 2016) $
#$Revision: 180515 $
#$URL: svn://www.crystallography.net/cod/cif/7/21/84/7218498.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_7218498
loop_
_publ_author_name
'Stratford, Samuel A.'
'Arhangelskis, Mihails'
'Bučar, Dejan-Krešimir'
'Jones, William'
_publ_section_title
;
 Solid-state photoreactivity of 9-substituted acridizinium bromide salts
;
_journal_issue                   47
_journal_name_full               CrystEngComm
_journal_page_first              10830
_journal_paper_doi               10.1039/C4CE01622J
_journal_volume                  16
_journal_year                    2014
_chemical_formula_moiety         'C13 H9 F N 1+, Br 1-, H2 O'
_chemical_formula_sum            'C13 H11 Br F N O'
_chemical_formula_weight         296.14
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_date             2013-07-16T17:12:53-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_cell_angle_alpha                90
_cell_angle_beta                 117.876(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   10.4896(4)
_cell_length_b                   12.9381(5)
_cell_length_c                   9.9423(3)
_cell_measurement_reflns_used    6927
_cell_measurement_temperature    270(2)
_cell_measurement_theta_max      25.35
_cell_measurement_theta_min      1.00
_cell_volume                     1192.75(8)
_computing_cell_refinement       'HKL Scalepack (Otwinowski & Minor 1997)'
_computing_data_collection       'Collect (Nonius B.V. 1998)'
_computing_data_reduction
;
 HKL Denzo and Scalepack (Otwinowski & Minor 1997)
;
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      270(2)
_diffrn_measured_fraction_theta_full 0.984
_diffrn_measured_fraction_theta_max 0.984
_diffrn_measurement_device_type  'Nonius Kappa CCD'
_diffrn_measurement_method       'Thin slice ω and φ scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0462
_diffrn_reflns_av_unetI/netI     0.0477
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            9072
_diffrn_reflns_theta_full        25.35
_diffrn_reflns_theta_max         25.35
_diffrn_reflns_theta_min         3.84
_exptl_absorpt_coefficient_mu    3.441
_exptl_absorpt_correction_T_max  0.719
_exptl_absorpt_correction_T_min  0.623
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
multi-scan from symmetry-related measurements 
 Sortav (Blessing 1995)
;
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.649
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             592
_exptl_crystal_size_max          0.14
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.748
_refine_diff_density_min         -0.318
_refine_diff_density_rms         0.054
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.062
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     170
_refine_ls_number_reflns         2153
_refine_ls_number_restraints     3
_refine_ls_restrained_S_all      1.061
_refine_ls_R_factor_all          0.0643
_refine_ls_R_factor_gt           0.0391
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0528P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0988
_refine_ls_wR_factor_ref         0.1032
_reflns_number_gt                1406
_reflns_number_total             2153
_reflns_threshold_expression     >2σ(I)
_cod_data_source_file            c4ce01622j2.cif
_cod_data_source_block           9-F
_cod_depositor_comments
'Adding full bibliography for 7218498--7218505.cif.'
_cod_original_cell_volume        1192.75(7)
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               7218498
loop_
_symmetry_equiv_pos_as_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Br1 Br 0.27235(5) 0.10783(3) 0.32507(5) 0.0754(2) Uani 1 1 d . . .
C5A C 0.2750(4) 0.1244(2) 0.8979(4) 0.0612(8) Uani 0.5 1 d P A 1
N1A N 0.2740(4) 0.1242(2) 0.7565(4) 0.0619(9) Uani 0.5 1 d P A 1
C9A C 0.7889(5) 0.1450(3) 1.1524(5) 0.0719(10) Uani 0.5 1 d P A 1
F1A F 0.9097(5) 0.1512(5) 1.2713(6) 0.1072(16) Uani 0.5 1 d P A 1
C10A C 0.7881(4) 0.1438(3) 1.0091(5) 0.0700(11) Uani 0.5 1 d P A 1
H10A H 0.8753 0.1474 1.0062 0.084 Uiso 0.5 1 calc PR A 1
N1B N 0.2750(4) 0.1244(2) 0.8979(4) 0.0612(8) Uani 0.5 1 d P A 2
C5B C 0.2740(4) 0.1242(2) 0.7565(4) 0.0619(9) Uani 0.5 1 d P A 2
C9B C 0.7881(4) 0.1438(3) 1.0091(5) 0.0700(11) Uani 0.5 1 d P A 2
C10B C 0.7889(5) 0.1450(3) 1.1524(5) 0.0719(10) Uani 0.5 1 d P A 2
H10B H 0.8762 0.1489 1.2413 0.086 Uiso 0.5 1 calc PR A 2
F1B F 0.9135(5) 0.1490(5) 1.0139(6) 0.1109(17) Uani 0.5 1 d P A 2
C6 C 0.4031(4) 0.1300(2) 1.0285(4) 0.0599(9) Uani 1 1 d . . .
H6 H 0.4022 0.1304 1.1216 0.072 Uiso 1 1 calc R A 1
C4 C 0.1426(5) 0.1178(3) 0.9002(5) 0.0714(11) Uani 1 1 d . . .
H4 H 0.1416 0.1178 0.9932 0.086 Uiso 1 1 calc R A 1
C1 C 0.1413(5) 0.1192(3) 0.6243(5) 0.0748(11) Uani 1 1 d . . .
H1 H 0.1406 0.1203 0.5305 0.09 Uiso 1 1 calc R A 1
C13 C 0.4027(4) 0.1288(2) 0.7528(4) 0.0626(10) Uani 1 1 d . . .
H13 H 0.4022 0.1276 0.659 0.075 Uiso 1 1 calc R A 1
C8 C 0.6653(4) 0.1406(3) 1.1608(4) 0.0646(10) Uani 1 1 d . . .
H8 H 0.6667 0.1412 1.2551 0.078 Uiso 1 1 calc R A 1
C7 C 0.5339(4) 0.1351(2) 1.0272(4) 0.0523(9) Uani 1 1 d . A .
C3 C 0.0176(5) 0.1115(3) 0.7715(5) 0.0822(12) Uani 1 1 d . A .
H3 H -0.0684 0.1061 0.7766 0.099 Uiso 1 1 calc R . .
C2 C 0.0150(5) 0.1128(3) 0.6272(6) 0.0858(13) Uani 1 1 d . A .
H2 H -0.0716 0.1093 0.5376 0.103 Uiso 1 1 calc R . .
C12 C 0.5332(4) 0.1349(2) 0.8833(4) 0.0579(9) Uani 1 1 d . A .
C11 C 0.6669(4) 0.1378(3) 0.8800(5) 0.0692(10) Uani 1 1 d . . .
H11 H 0.6691 0.1355 0.7877 0.083 Uiso 1 1 calc R A 1
O1 O 0.6343(4) 0.1134(2) 0.4850(5) 0.0995(11) Uani 1 1 d D . .
H1O H 0.552(4) 0.099(3) 0.425(6) 0.119 Uiso 1 1 d D . .
H2O H 0.656(4) 0.063(3) 0.539(5) 0.119 Uiso 1 1 d D . .
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 0 '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 0.006 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.2901 2.4595 '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
C6 C5A N1A 119.7(3)
C6 C5A C4 122.0(3)
N1A C5A C4 118.2(4)
C13 N1A C1 122.5(3)
C13 N1A C5A 118.8(3)
C1 N1A C5A 118.7(3)
F1A C9A C8 121.3(4)
F1A C9A C10A 118.0(4)
C8 C9A C10A 120.7(4)
C11 C10A C9A 121.8(4)
C11 C10A H10A 119.1
C9A C10A H10A 119.1
C5A C6 C7 122.3(3)
C5A C6 H6 118.8
C7 C6 H6 118.8
C3 C4 C5A 121.5(4)
C3 C4 H4 119.2
C5A C4 H4 119.2
C2 C1 N1A 122.8(4)
C2 C1 H1 118.6
N1A C1 H1 118.6
N1A C13 C12 122.3(3)
N1A C13 H13 118.8
C12 C13 H13 118.8
C9A C8 C7 119.7(4)
C9A C8 H8 120.2
C7 C8 H8 120.2
C6 C7 C8 122.4(3)
C6 C7 C12 118.1(3)
C8 C7 C12 119.6(3)
C4 C3 C2 120.8(4)
C4 C3 H3 119.6
C2 C3 H3 119.6
C1 C2 C3 118.0(5)
C1 C2 H2 121
C3 C2 H2 121
C13 C12 C11 122.5(3)
C13 C12 C7 118.7(3)
C11 C12 C7 118.8(4)
C10A C11 C12 119.5(4)
C10A C11 H11 120.3
C12 C11 H11 120.3
H1O O1 H2O 101(3)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C5A C6 1.366(5)
C5A N1A 1.401(5)
C5A C4 1.401(5)
N1A C13 1.370(5)
N1A C1 1.399(6)
C9A F1A 1.268(6)
C9A C8 1.340(6)
C9A C10A 1.421(5)
C10A C11 1.321(5)
C10A H10A 0.93
C6 C7 1.380(5)
C6 H6 0.93
C4 C3 1.339(6)
C4 H4 0.93
C1 C2 1.341(6)
C1 H1 0.93
C13 C12 1.380(5)
C13 H13 0.93
C8 C7 1.399(5)
C8 H8 0.93
C7 C12 1.427(5)
C3 C2 1.422(6)
C3 H3 0.93
C2 H2 0.93
C12 C11 1.418(5)
C11 H11 0.93
O1 H1O 0.81(4)
O1 H2O 0.80(4)
