#------------------------------------------------------------------------------
#$Date: 2016-02-20 02:53:41 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176768 $
#$URL: svn://www.crystallography.net/cod/cif/2/10/59/2105986.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided by IUCr Journals, http://journals.iucr.org/.
#
# The file may be used within the scientific community so long as
# proper attribution is given to the journal article from which the
# data were obtained.
#
data_2105986
loop_
_publ_author_name
'Poulain, Agnieszka'
'Kubicki, Maciej'
'Lecomte, Claude'
_publ_section_title
;
 Isomorphism and solid solution as shown by an accurate high-resolution
 diffraction experiment
;
_journal_coeditor_code           GW5032
_journal_issue                   6
_journal_name_full               'Acta Crystallographica Section B'
_journal_page_first              973
_journal_page_last               982
_journal_paper_doi               10.1107/S2052520614021325
_journal_volume                  70
_journal_year                    2014
_chemical_formula_moiety         'C10.98 H7 Br0.02 Cl N3.98 O2'
_chemical_formula_sum            'C10.98 H7 Br0.02 Cl N3.98 O2'
_chemical_formula_weight         263.933
_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           MoPro
_cell_angle_alpha                90.00
_cell_angle_beta                 105.428(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   9.3618(2)
_cell_length_b                   9.6497(2)
_cell_length_c                   12.9909(2)
_cell_measurement_reflns_used    29906
_cell_measurement_temperature    100
_cell_measurement_theta_max      53.1590
_cell_measurement_theta_min      3.0844
_cell_volume                     1131.29(4)
_computing_structure_refinement  'MoPro (J. Appl. Cryst. 2005, 38, 38-54)'
_diffrn_ambient_temperature      100
_diffrn_detector_area_resol_mean 16.1544
_diffrn_measured_fraction_theta_full 0.961
_diffrn_measured_fraction_theta_max 0.737
_diffrn_measurement_device_type  'Xcalibur, Eos'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'Enhance (Mo) X-ray Source'
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.7107
_diffrn_reflns_av_sigmaI/netI    0.02578
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            104943
_diffrn_reflns_theta_full        25.61
_diffrn_reflns_theta_max         53.31
_diffrn_reflns_theta_min         3.09
_exptl_absorpt_coefficient_mu    0.407
_exptl_absorpt_correction_T_max  0.952
_exptl_absorpt_correction_T_min  0.816
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.4 (release 09-12-2010 CrysAlis171 .NET)
(compiled Dec  9 2010,10:47:41)
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)
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.550
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             537.8
_exptl_crystal_size_max          0.78
_exptl_crystal_size_mid          0.60
_exptl_crystal_size_min          0.15
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.122
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     477
_refine_ls_number_reflns         10032
_refine_ls_number_restraints     27
_refine_ls_restrained_S_all      2.339
_refine_ls_R_factor_all          0.0210
_refine_ls_R_factor_gt           0.0209
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef F
_refine_ls_weighting_scheme      sigma
_refine_ls_wR_factor_gt          0.0217
_refine_ls_wR_factor_ref         0.0217
_reflns_number_gt                10015
_reflns_number_total             10032
_reflns_threshold_expression     >2.0sigma(I)
_cod_data_source_file            gw5032sup1.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               2105986
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_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_occupancy
_atom_site_disorder_group
C C1 0.71915(3) 0.44793(3) 0.75344(2) 0.01131(2) Uani d 1 .
C C2 0.84128(3) 0.38278(3) 0.73277(2) 0.01392(2) Uani d 1 .
C C3 0.86833(3) 0.39882(3) 0.63296(2) 0.01489(2) Uani d 1 .
C C4 0.77406(3) 0.48337(3) 0.55774(2) 0.01306(2) Uani d 1 .
C C5 0.65630(3) 0.55373(3) 0.58015(2) 0.01384(2) Uani d 1 .
C C6 0.62685(3) 0.53391(3) 0.67857(2) 0.01331(2) Uani d 1 .
C C7 0.57637(3) 0.33046(3) 0.86576(2) 0.01258(2) Uani d 1 .
C C71 0.48373(4) 0.24652(3) 0.77730(2) 0.01737(2) Uani d 1 .
C C8 0.66896(3) 0.42395(3) 1.01645(2) 0.01295(2) Uani d 1 .
C C9 0.74268(3) 0.48420(3) 0.94911(2) 0.012440(10) Uani d 1 .
N N1 0.68249(3) 0.42148(3) 0.85209(2) 0.011670(10) Uani d 1 .
N N2 0.56687(3) 0.33063(3) 0.96562(2) 0.01357(2) Uani d 1 .
N N8 0.69211(3) 0.45406(3) 1.12789(2) 0.01603(2) Uani d 1 .
O O81 0.61294(4) 0.39555(4) 1.17567(2) 0.02293(3) Uani d 1 .
O O82 0.78994(5) 0.53705(5) 1.16821(3) 0.02337(3) Uani d 1 .
Cl CL1 0.79800(2) 0.49908(2) 0.430950(10) 0.0191720(10) Uani d 1 .
H H72 0.41362 0.31322 0.72122 0.03798 Uani d 1 .
H H71 0.41757 0.18040 0.81066 0.04218 Uani d 1 .
H H73 0.55160 0.18772 0.74017 0.03877 Uani d 1 .
H H6 0.53143 0.58139 0.69650 0.02815 Uani d 1 .
H H2 0.91314 0.32126 0.79523 0.03019 Uani d 1 .
H H3 0.95545 0.34280 0.61023 0.03351 Uani d 1 .
H H5 0.58701 0.62160 0.52114 0.03150 Uani d 1 .
Br BR1a 0.8794(2) 0.6396(2) 0.96770(10) 0.02149(4) Uani d 0.02 2
C C91b 0.85026(3) 0.58946(3) 0.96423(2) 0.01565(2) Uani d 0.98 1
N N91b 0.93843(3) 0.67627(3) 0.97429(2) 0.02309(2) Uani d 0.98 1
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
'Clementi & Roetti 1974. Atomic Data & Nuclear Data Tables. 14, 177'
H H 0.0000 0.0000
'Clementi & Roetti 1974. Atomic Data & Nuclear Data Tables. 14, 177'
N N 0.0061 0.0033
'Clementi & Roetti 1974. Atomic Data & Nuclear Data Tables. 14, 177'
O O 0.0106 0.0060
'Clementi & Roetti 1974. Atomic Data & Nuclear Data Tables. 14, 177'
Cl Cl 0.1484 0.1585
'Clementi & Roetti 1974. Atomic Data & Nuclear Data Tables. 14, 177'
Br Br -0.2901 2.4595
'Clementi & Roetti 1974. Atomic Data & Nuclear Data Tables. 14, 177'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
C1 N1 C9 127.06(2)
C1 N1 C7 125.64(3)
C1 C6 C5 119.12(3)
C1 C6 H6 119.8
C1 C2 C3 119.40(3)
C1 C2 H2 118.8
C2 C1 N1 119.72(3)
C2 C1 C6 121.59(3)
C2 C3 C4 118.65(3)
C2 C3 H3 122.3
C3 C4 CL1 120.11(3)
C3 C4 C5 121.94(3)
C3 C2 H2 121.8
C4 C5 C6 119.18(3)
C4 C5 H5 120.4
C4 C3 H3 118.9
C5 C4 CL1 117.92(2)
C5 C6 H6 121.1
C6 C1 N1 118.62(2)
C6 C5 H5 120.4
C7 N1 C9 107.28(2)
C7 N2 C8 104.86(2)
C7 C71 H72 109.2
C7 C71 H73 110.3
C7 C71 H71 107.3
C71 C7 N1 122.93(2)
C71 C7 N2 125.61(2)
C8 N8 O81 117.95(3)
C8 N8 O82 117.32(3)
C8 C9 BR1a 132.09(6)
C8 C9 N1 104.09(2)
C8 C9 C91b 132.57(3)
C9 C8 N8 126.00(3)
C9 C8 N2 112.31(3)
C9 C91b N91b 178.50(3)
N1 C9 BR1a 123.28(5)
N1 C9 C91b 123.28(2)
N1 C7 N2 111.45(2)
N2 C8 N8 121.68(3)
O81 N8 O82 124.73(4)
H72 C71 H73 110.4
H72 C71 H71 109.0
H71 C71 H73 110.5
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C1 N1 1.4351(3)
C1 C6 1.3907(3)
C1 C2 1.3921(4)
C2 C3 1.3944(4)
C2 H2 1.083
C3 C4 1.3930(4)
C3 H3 1.083
C4 CL1 1.7270(3)
C4 C5 1.3900(4)
C5 C6 1.3910(4)
C5 H5 1.083
C6 H6 1.083
C7 N1 1.3725(3)
C7 N2 1.3238(3)
C7 C71 1.4827(3)
C71 H72 1.059
C71 H73 1.059
C71 H71 1.059
C8 N8 1.4355(3)
C8 N2 1.3508(4)
C8 C9 1.3786(4)
C9 BR1a 1.944(2)
C9 N1 1.3764(3)
C9 C91b 1.4069(4)
N8 O81 1.2240(4)
N8 O82 1.2244(5)
C91b N91b 1.1588(4)
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
C5 H5 N91b 4_575 1.083 2.379 3.3687(4) 151.2
C6 H6 O81 3_667 1.083 2.414 3.3690(4) 146.3
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
C1 N1 C9 BR1a 6.75(6)
C1 N1 C9 C8 179.21(2)
C1 N1 C9 C91b 1.65(2)
C1 N1 C7 N2 -178.99(2)
C1 N1 C7 C71 -0.28(2)
C1 C6 C5 C4 2.22(2)
C1 C6 C5 H5 -179.0
C1 C2 C3 C4 1.85(2)
C1 C2 C3 H3 -174.1
C2 C1 N1 C9 83.31(2)
C2 C1 N1 C7 -98.72(2)
C2 C1 C6 C5 0.86(2)
C2 C1 C6 H6 178.8
C2 C3 C4 CL1 -176.72(2)
C2 C3 C4 C5 1.25(2)
C3 C4 C5 C6 -3.31(2)
C3 C4 C5 H5 177.9
C3 C2 C1 N1 174.11(2)
C3 C2 C1 C6 -2.93(2)
C4 C5 C6 H6 -175.6
C4 C3 C2 H2 -177.8
C5 C4 C3 H3 177.3
C5 C6 C1 N1 -176.21(2)
C6 C1 N1 C9 -99.56(2)
C6 C1 N1 C7 78.42(2)
C6 C1 C2 H2 176.7
C6 C5 C4 CL1 174.70(2)
C7 N1 C9 BR1a -171.52(7)
C7 N1 C9 C8 0.94(2)
C7 N1 C9 C91b -176.63(2)
C7 N2 C8 N8 179.84(2)
C7 N2 C8 C9 0.53(2)
C71 C7 N1 C9 178.03(2)
C71 C7 N2 C8 -178.56(2)
C8 N2 C7 N1 0.11(2)
C8 C9 C91b N91b -168.85(3)
C9 N1 C7 N2 -0.69(2)
C9 C8 N8 O81 176.97(3)
C9 C8 N8 O82 -2.89(3)
N1 C9 C8 N8 179.80(2)
N1 C9 C8 N2 -0.93(2)
N1 C9 C91b N91b 7.94(3)
N1 C7 C71 H72 -66.2
N1 C7 C71 H73 55.3
N1 C7 C71 H71 175.8
N1 C1 C6 H6 1.7
N1 C1 C2 H2 -6.2
N2 C7 C71 H72 112.3
N2 C7 C71 H73 -126.1
N2 C7 C71 H71 -5.7
N2 C8 N8 O81 -2.24(3)
N2 C8 N8 O82 177.90(4)
N2 C8 C9 BR1a 170.57(6)
N2 C8 C9 C91b 176.31(2)
N8 C8 C9 BR1a -8.70(6)
N8 C8 C9 C91b -2.97(3)
CL1 C4 C5 H5 -4.1
CL1 C4 C3 H3 -0.6
H6 C6 C5 H5 3.2
H2 C2 C3 H3 6.2
