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#$Date: 2023-10-05 10:54:38 +0200 (Thu 05 de Oct de 2023) $
#$Revision: 286676 $
#$URL: svn://www.crystallography.net/cod/cif/8/10/75/8107585.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_8107585
loop_
_publ_author_name
'Adeloye, Adewale O.'
'Clayton, Hadley S.'
_publ_section_title
;
 Crystal structure of 1,10-phenanthrolinium bromide dihydrate, C12H9N2Br
;
_journal_issue                   5
_journal_name_full
'Zeitschrift für Kristallographie - New Crystal Structures'
_journal_page_first              867
_journal_page_last               869
_journal_paper_doi               10.1515/ncrs-2023-0244
_journal_volume                  238
_journal_year                    2023
_chemical_formula_moiety         'C12 H9 N2, Br, 2(H2 O)'
_chemical_formula_sum            'C12 H13 Br N2 O2'
_chemical_formula_weight         297.15
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   mixed
_cell_angle_alpha                98.235(9)
_cell_angle_beta                 101.744(8)
_cell_angle_gamma                111.005(7)
_cell_formula_units_Z            2
_cell_length_a                   7.4005(13)
_cell_length_b                   9.4122(16)
_cell_length_c                   9.7916(17)
_cell_measurement_reflns_used    6930
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      27.42
_cell_measurement_theta_min      2.19
_cell_volume                     605.69(19)
_computing_cell_refinement       'COSMO (Bruker, V1.61, 2009)'
_computing_data_collection       'COSMO (Bruker, V1.61, 2009)'
_computing_data_reduction        'SAINT (Bruker)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXS-2013 (Sheldrick, 2008)'
_diffrn_ambient_temperature      100.15
_diffrn_detector                 'Bruker APEX2 area detector'
_diffrn_detector_area_resol_mean 7.9
_diffrn_detector_type            'CCD area detector'
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.988
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  'Bruker SMART APEX2 area detector'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0297
_diffrn_reflns_av_unetI/netI     0.0279
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.988
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            10251
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.988
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.487
_diffrn_reflns_theta_min         2.186
_diffrn_source                   'sealed X-ray tube'
_diffrn_source_type              'sealed X-ray tube'
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    3.385
_exptl_absorpt_correction_T_max  0.7455
_exptl_absorpt_correction_T_min  0.5516
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Bruker)'
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.629
_exptl_crystal_density_meas      .
_exptl_crystal_description       block
_exptl_crystal_F_000             300
_exptl_crystal_recrystallization_method
;
 'The material was recrystallised from a mixture of methanol and water  by slow
 evaporation'
;
_exptl_crystal_size_max          0.38
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.16
_refine_diff_density_max         0.337
_refine_diff_density_min         -0.306
_refine_diff_density_rms         0.062
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.056
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     172
_refine_ls_number_reflns         2743
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.056
_refine_ls_R_factor_all          0.0229
_refine_ls_R_factor_gt           0.0209
_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)+(0.0180P)²+0.3893P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0507
_refine_ls_wR_factor_ref         0.0514
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2596
_reflns_number_total             2743
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            suppl_j_ncrs-2023-0244_suppl_001.cif
_cod_data_source_block           mo_pa_aa_pa_0m
_cod_original_cell_volume        605.69(18)
_cod_database_code               8107585
_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.
;
_shelx_estimated_absorpt_t_max   0.613
_shelx_estimated_absorpt_t_min   0.360
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
 At 1.5 times of:
  All O(H,H) groups
2. Others
 Fixed Sof: O2(0.5) H2A(0.5) H2B(0.5) O3(0.5) H3A(0.5) H3B(0.5)
3.a Riding coordinates:
 N1(H1)
3.b Free rotating group:
 O1(H1A,H1B), O2(H2A,H2B), O3(H3A,H3B)
3.c Aromatic/amide H refined with riding coordinates:
 C7(H7), C10(H10), C4(H4), C12(H12), C5(H5), C8(H8), C11(H11), C3(H3)
;
loop_
_space_group_symop_operation_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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Br1 Br 0.27857(3) 0.11119(2) 0.39455(2) 0.01755(6) Uani 1 1 d . . . . .
C1 C 0.2385(2) 0.53193(18) 0.09434(17) 0.0127(3) Uani 1 1 d . . . . .
C2 C 0.2639(2) 0.50116(19) -0.04636(17) 0.0127(3) Uani 1 1 d . . . . .
C3 C 0.3853(3) 0.5947(2) -0.2254(2) 0.0239(4) Uani 1 1 d . . . . .
H3 H 0.452233 0.680111 -0.263100 0.029 Uiso 1 1 calc R . . . .
C4 C 0.3189(3) 0.4420(2) -0.3101(2) 0.0245(4) Uani 1 1 d . . . . .
H4 H 0.342367 0.426193 -0.401814 0.029 Uiso 1 1 calc R . . . .
C5 C 0.2205(3) 0.3168(2) -0.25956(18) 0.0201(4) Uani 1 1 d . . . . .
H5 H 0.173606 0.213046 -0.315849 0.024 Uiso 1 1 calc R . . . .
C6 C 0.1895(2) 0.34372(19) -0.12275(17) 0.0146(3) Uani 1 1 d . . . . .
C7 C 0.0864(3) 0.2206(2) -0.06086(19) 0.0177(3) Uani 1 1 d . . . . .
H7 H 0.034209 0.114959 -0.113832 0.021 Uiso 1 1 calc R . . . .
C8 C 0.0620(3) 0.2519(2) 0.07111(19) 0.0184(4) Uani 1 1 d . . . . .
H8 H -0.007522 0.168157 0.109724 0.022 Uiso 1 1 calc R . . . .
C9 C 0.1397(2) 0.4098(2) 0.15393(17) 0.0150(3) Uani 1 1 d . . . . .
C10 C 0.1217(3) 0.4493(2) 0.29392(19) 0.0221(4) Uani 1 1 d . . . . .
H10 H 0.054542 0.368921 0.336870 0.027 Uiso 1 1 calc R . . . .
C11 C 0.2008(3) 0.6029(3) 0.36799(19) 0.0269(4) Uani 1 1 d . . . . .
H11 H 0.190301 0.629276 0.462577 0.032 Uiso 1 1 calc R . . . .
C12 C 0.2961(3) 0.7194(2) 0.3037(2) 0.0245(4) Uani 1 1 d . . . . .
H12 H 0.350287 0.826140 0.354079 0.029 Uiso 1 1 calc R . . . .
N1 N 0.3119(2) 0.68247(17) 0.17224(15) 0.0176(3) Uani 1 1 d . . . . .
H1 H 0.369124 0.755292 0.132193 0.021 Uiso 1 1 d R . . . .
N2 N 0.3598(2) 0.62597(17) -0.09655(16) 0.0181(3) Uani 1 1 d . . . . .
O1 O 0.8326(2) 1.11613(18) 0.37689(15) 0.0307(3) Uani 1 1 d . . . . .
H1A H 0.945807 1.112674 0.376812 0.046 Uiso 1 1 d G . . . .
H1B H 0.793038 1.063350 0.436555 0.046 Uiso 1 1 d G . . . .
O2 O 0.4789(4) 0.9793(3) 0.1546(3) 0.0180(6) Uani 0.5 1 d . . P A 1
H2A H 0.597107 1.018192 0.211287 0.027 Uiso 0.5 1 d G . P A 1
H2B H 0.414019 1.021318 0.196234 0.027 Uiso 0.5 1 d G . P A 1
O3 O 0.5536(7) 0.9525(4) 0.1155(4) 0.0410(9) Uani 0.5 1 d . . P B 2
H3A H 0.625915 1.028255 0.187770 0.061 Uiso 0.5 1 d G . P B 2
H3B H 0.516342 0.995625 0.051017 0.061 Uiso 0.5 1 d G . P B 2
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'
Br Br -0.2901 2.4595 '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
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
C1 N1 H1 117.2 . .
C12 N1 H1 119.9 . .
C12 N1 C1 122.88(16) . .
C3 N2 C2 116.42(15) . .
C1 C9 C10 117.94(16) . .
C1 C9 C8 118.88(15) . .
C10 C9 C8 123.19(16) . .
N1 C1 C9 119.19(15) . .
N1 C1 C2 119.64(15) . .
C9 C1 C2 121.17(15) . .
C6 C7 H7 119.4 . .
C8 C7 H7 119.4 . .
C8 C7 C6 121.18(16) . .
N2 C2 C1 117.47(15) . .
N2 C2 C6 124.45(15) . .
C6 C2 C1 118.07(15) . .
C9 C10 H10 119.8 . .
C11 C10 C9 120.31(18) . .
C11 C10 H10 119.8 . .
C2 C6 C7 119.90(15) . .
C5 C6 C7 123.23(16) . .
C5 C6 C2 116.86(16) . .
C5 C4 H4 120.2 . .
C5 C4 C3 119.53(17) . .
C3 C4 H4 120.2 . .
N1 C12 H12 119.9 . .
N1 C12 C11 120.26(17) . .
C11 C12 H12 119.9 . .
C6 C5 H5 120.5 . .
C4 C5 C6 118.96(17) . .
C4 C5 H5 120.5 . .
C9 C8 H8 119.6 . .
C7 C8 C9 120.77(16) . .
C7 C8 H8 119.6 . .
C10 C11 C12 119.42(17) . .
C10 C11 H11 120.3 . .
C12 C11 H11 120.3 . .
N2 C3 C4 123.78(17) . .
N2 C3 H3 118.1 . .
C4 C3 H3 118.1 . .
H1A O1 H1B 104.5 . .
H2A O2 H2B 104.5 . .
H3A O3 H3B 104.5 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
N1 H1 0.8599 .
N1 C1 1.362(2) .
N1 C12 1.324(2) .
N2 C2 1.355(2) .
N2 C3 1.321(2) .
C9 C1 1.400(2) .
C9 C10 1.414(2) .
C9 C8 1.432(2) .
C1 C2 1.431(2) .
C7 H7 0.9500 .
C7 C6 1.431(2) .
C7 C8 1.346(3) .
C2 C6 1.410(2) .
C10 H10 0.9500 .
C10 C11 1.371(3) .
C6 C5 1.407(2) .
C4 H4 0.9500 .
C4 C5 1.365(3) .
C4 C3 1.407(3) .
C12 H12 0.9500 .
C12 C11 1.386(3) .
C5 H5 0.9500 .
C8 H8 0.9500 .
C11 H11 0.9500 .
C3 H3 0.9500 .
O1 H1A 0.8501 .
O1 H1B 0.8499 .
O2 H2A 0.8499 .
O2 H2B 0.8501 .
O3 H3A 0.8501 .
O3 H3B 0.8499 .
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
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
N1 C1 C2 N2 -0.7(2) . . . .
N1 C1 C2 C6 178.74(14) . . . .
N1 C12 C11 C10 -0.5(3) . . . .
N2 C2 C6 C7 -178.64(15) . . . .
N2 C2 C6 C5 0.7(2) . . . .
C9 C1 C2 N2 179.51(15) . . . .
C9 C1 C2 C6 -1.1(2) . . . .
C9 C10 C11 C12 0.9(3) . . . .
C1 N1 C12 C11 -0.3(3) . . . .
C1 C9 C10 C11 -0.5(3) . . . .
C1 C9 C8 C7 1.2(3) . . . .
C1 C2 C6 C7 2.0(2) . . . .
C1 C2 C6 C5 -178.67(15) . . . .
C7 C6 C5 C4 179.33(16) . . . .
C2 N2 C3 C4 0.1(3) . . . .
C2 C6 C5 C4 0.0(2) . . . .
C10 C9 C1 N1 -0.3(2) . . . .
C10 C9 C1 C2 179.51(15) . . . .
C10 C9 C8 C7 -178.83(17) . . . .
C6 C7 C8 C9 -0.3(3) . . . .
C12 N1 C1 C9 0.7(2) . . . .
C12 N1 C1 C2 -179.09(15) . . . .
C5 C4 C3 N2 0.6(3) . . . .
C8 C9 C1 N1 179.69(14) . . . .
C8 C9 C1 C2 -0.5(2) . . . .
C8 C9 C10 C11 179.54(16) . . . .
C8 C7 C6 C2 -1.3(3) . . . .
C8 C7 C6 C5 179.34(17) . . . .
C3 N2 C2 C1 178.66(15) . . . .
C3 N2 C2 C6 -0.7(2) . . . .
C3 C4 C5 C6 -0.6(3) . . . .
