#------------------------------------------------------------------------------
#$Date: 2019-11-07 21:56:27 +0200 (Thu, 07 Nov 2019) $
#$Revision: 223656 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/23/20/7232082.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_7232082
loop_
_publ_author_name
'Sharara, Kudzaishe N.'
'Nyamayaro, Kudzanai'
'Wicht, Merrill M.'
'Venter, Gerhard A.'
'Báthori, Nikoletta B.'
_publ_section_title
;
 Multicomponent crystals of nitrofurazone -- when more is less
;
_journal_issue                   7
_journal_name_full               CrystEngComm
_journal_page_first              1091
_journal_paper_doi               10.1039/C8CE01911H
_journal_volume                  21
_journal_year                    2019
_chemical_formula_sum            'C6 H6 N4 O4'
_chemical_formula_weight         198.15
_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   mixed
_audit_creation_method           SHELXL-2016/4
_audit_update_record
;
2018-11-06 deposited with the CCDC.
2019-01-03 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 103.134(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   13.4449(14)
_cell_length_b                   7.8221(9)
_cell_length_c                   7.8587(9)
_cell_measurement_reflns_used    1710
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      28.423
_cell_measurement_theta_min      3.034
_cell_volume                     804.86(16)
_computing_structure_refinement  'SHELXL-2016/4 (Sheldrick, 2016)'
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker APEX II'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0310
_diffrn_reflns_av_unetI/netI     0.0149
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            19287
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.423
_diffrn_reflns_theta_min         3.034
_exptl_absorpt_coefficient_mu    0.140
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.889
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS, Bruker ASX'
_exptl_crystal_colour            orange
_exptl_crystal_density_diffrn    1.635
_exptl_crystal_description       prism
_exptl_crystal_F_000             408
_exptl_crystal_size_max          0.250
_exptl_crystal_size_mid          0.250
_exptl_crystal_size_min          0.100
_refine_diff_density_max         0.249
_refine_diff_density_min         -0.269
_refine_diff_density_rms         0.045
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.047
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     139
_refine_ls_number_reflns         2029
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.047
_refine_ls_R_factor_all          0.0423
_refine_ls_R_factor_gt           0.0333
_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)+(0.0438P)²+0.2417P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0826
_refine_ls_wR_factor_ref         0.0892
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1710
_reflns_number_total             2029
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            c8ce01911h2.cif
_cod_data_source_block           gamma_LT
_cod_depositor_comments
'Adding full bibliography for 7232079--7232083.cif.'
_cod_database_code               7232082
_shelx_shelxl_version_number     2016/4
_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_min   0.966
_shelx_estimated_absorpt_t_max   0.986
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 0.12911(7) -0.04158(12) 0.60673(13) 0.0233(2) Uani 1 1 d . .
O2 O 0.17835(8) -0.15272(11) 0.55202(14) 0.0367(3) Uani 1 1 d . .
O3 O 0.05863(7) -0.07061(12) 0.67852(12) 0.0325(2) Uani 1 1 d . .
C4 C 0.15314(8) 0.13205(14) 0.58685(14) 0.0194(2) Uani 1 1 d . .
O5 O 0.23528(6) 0.16265(9) 0.51976(10) 0.01901(18) Uani 1 1 d . .
C6 C 0.24271(8) 0.33738(13) 0.51504(14) 0.0188(2) Uani 1 1 d . .
C7 C 0.16652(9) 0.41145(15) 0.57850(15) 0.0226(2) Uani 1 1 d . .
H7 H 0.155126 0.530440 0.589131 0.027 Uiso 1 1 calc R U
C8 C 0.10796(9) 0.27685(15) 0.62526(15) 0.0234(2) Uani 1 1 d . .
H8 H 0.049434 0.286108 0.673356 0.028 Uiso 1 1 calc R U
C9 C 0.32371(8) 0.39983(13) 0.44013(14) 0.0191(2) Uani 1 1 d . .
H9 H 0.367587 0.322163 0.399793 0.023 Uiso 1 1 calc R U
N10 N 0.33617(7) 0.56153(12) 0.42829(12) 0.0192(2) Uani 1 1 d . .
N11 N 0.41299(7) 0.60980(11) 0.35289(12) 0.0206(2) Uani 1 1 d . .
H11 H 0.4508(12) 0.537(2) 0.310(2) 0.035(4) Uiso 1 1 d . .
C12 C 0.43639(9) 0.77904(14) 0.34366(15) 0.0208(2) Uani 1 1 d . .
O13 O 0.51103(7) 0.81862(11) 0.28499(13) 0.0311(2) Uani 1 1 d . .
N14 N 0.37655(9) 0.89067(13) 0.40041(15) 0.0284(2) Uani 1 1 d . .
H15 H 0.3931(13) 0.993(3) 0.404(2) 0.049(5) Uiso 1 1 d . .
H14 H 0.3226(14) 0.854(2) 0.442(2) 0.045(5) Uiso 1 1 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 0.0000 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'
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
O2 N1 O3 124.27(10)
O2 N1 C4 119.12(10)
O3 N1 C4 116.60(10)
O5 C4 C8 112.83(10)
O5 C4 N1 116.23(10)
C8 C4 N1 130.94(11)
C4 O5 C6 104.99(8)
C7 C6 O5 110.34(9)
C7 C6 C9 134.97(10)
O5 C6 C9 114.63(10)
C6 C7 C8 106.70(10)
C6 C7 H7 126.7
C8 C7 H7 126.7
C4 C8 C7 105.15(10)
C4 C8 H8 127.4
C7 C8 H8 127.4
N10 C9 C6 119.28(10)
N10 C9 H9 120.4
C6 C9 H9 120.4
C9 N10 N11 115.56(10)
N10 N11 C12 120.02(9)
N10 N11 H11 123.4(11)
C12 N11 H11 116.6(11)
O13 C12 N14 124.39(11)
O13 C12 N11 118.62(10)
N14 C12 N11 116.98(10)
C12 N14 H15 117.9(13)
C12 N14 H14 120.5(11)
H15 N14 H14 121.4(17)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
N1 O2 1.2281(13)
N1 O3 1.2291(13)
N1 C4 1.4129(14)
C4 O5 1.3488(13)
C4 C8 1.3514(16)
O5 C6 1.3715(13)
C6 C7 1.3660(16)
C6 C9 1.4362(15)
C7 C8 1.4124(16)
C7 H7 0.9500
C8 H8 0.9500
C9 N10 1.2821(14)
C9 H9 0.9500
N10 N11 1.3559(13)
N11 C12 1.3664(14)
N11 H11 0.882(17)
C12 O13 1.2352(14)
C12 N14 1.3311(15)
N14 H15 0.830(19)
N14 H14 0.906(19)
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
O2 N1 C4 O5 -5.01(15)
O3 N1 C4 O5 175.27(9)
O2 N1 C4 C8 175.63(12)
O3 N1 C4 C8 -4.09(18)
C8 C4 O5 C6 -0.08(12)
N1 C4 O5 C6 -179.56(9)
C4 O5 C6 C7 0.13(12)
C4 O5 C6 C9 -177.49(9)
O5 C6 C7 C8 -0.13(13)
C9 C6 C7 C8 176.80(12)
O5 C4 C8 C7 0.00(13)
N1 C4 C8 C7 179.38(11)
C6 C7 C8 C4 0.08(13)
C7 C6 C9 N10 2.5(2)
O5 C6 C9 N10 179.29(10)
C6 C9 N10 N11 -178.73(9)
C9 N10 N11 C12 -176.08(10)
N10 N11 C12 O13 175.19(10)
N10 N11 C12 N14 -4.39(16)
