#------------------------------------------------------------------------------
#$Date: 2021-04-21 07:21:11 +0200 (Wed 21 de Apr de 2021) $
#$Revision: 264353 $
#$URL: svn://www.crystallography.net/cod/cif/1/56/19/1561945.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_1561945
loop_
_publ_author_name
'Noland, Wayland E.'
'Herzig, Ryan J.'
'Fox, Renee C.'
'Tritch, Kenneth J.'
_publ_section_title
;
 3,5-Dibromo-4-carbamoylbenzoic acid 2-propanol monosolvate
;
_journal_coeditor_code           HB4381
_journal_issue                   4
_journal_name_full               IUCrData
_journal_page_first              x210391
_journal_paper_doi               10.1107/S2414314621003916
_journal_volume                  6
_journal_year                    2021
_chemical_formula_iupac          'C8 H5 Br2 N O3, C3 H8 O'
_chemical_formula_moiety         'C8 H5 Br2 N O3, C3 H8 O'
_chemical_formula_sum            'C11 H13 Br2 N O4'
_chemical_formula_weight         383.04
_chemical_melting_point          528
_chemical_name_common            I
_chemical_name_systematic
;
3,5-Dibromo-4-carbamoylbenzoic acid 2-propanol monosolvate
;
_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
_audit_creation_method           SHELXL-2018/3
_cell_angle_alpha                71.3760(10)
_cell_angle_beta                 81.7450(10)
_cell_angle_gamma                83.6820(10)
_cell_formula_units_Z            2
_cell_length_a                   7.2866(5)
_cell_length_b                   8.5212(6)
_cell_length_c                   12.1832(8)
_cell_measurement_reflns_used    2971
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      27.28
_cell_measurement_theta_min      2.60
_cell_volume                     707.76(8)
_computing_cell_refinement
;
SAINT (Bruker, 2018)
;
_computing_data_collection
;
APEX3 (Bruker, 2018)
;
_computing_data_reduction
;
SAINT (Bruker, 2018)
;
_computing_molecular_graphics
;
Mercury (Macrae et al., 2020)
;
_computing_publication_material
;
PublCIF (Westrip, 2010)
;
_computing_structure_refinement
;
SHELXL2018/3 (Sheldrick, 2015b)
;
_computing_structure_solution
;
SHELXT2014 (Sheldrick, 2015a)
;
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.981
_diffrn_measurement_device_type  'Bruker APEXII CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0213
_diffrn_reflns_av_unetI/netI     0.0231
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            8139
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.306
_diffrn_reflns_theta_min         1.776
_diffrn_source                   'sealed tube'
_exptl_absorpt_coefficient_mu    5.732
_exptl_absorpt_correction_T_max  0.7455
_exptl_absorpt_correction_T_min  0.4855
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(SADABS; Krause et al.,  2015)
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.797
_exptl_crystal_description       block
_exptl_crystal_F_000             376
_exptl_crystal_size_max          0.400
_exptl_crystal_size_mid          0.380
_exptl_crystal_size_min          0.160
_refine_diff_density_max         0.633
_refine_diff_density_min         -0.901
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.037
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     201
_refine_ls_number_reflns         3128
_refine_ls_number_restraints     151
_refine_ls_restrained_S_all      1.014
_refine_ls_R_factor_all          0.0326
_refine_ls_R_factor_gt           0.0262
_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)+(0.0296P)²+0.5063P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0622
_refine_ls_wR_factor_ref         0.0649
_reflns_number_gt                2683
_reflns_number_total             3128
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            hb4381sup1.cif
_cod_data_source_block           I
_cod_database_code               1561945
_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   0.208
_shelx_estimated_absorpt_t_max   0.461
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'
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_assembly
_atom_site_disorder_group
Br Br1 0.61784(4) 0.53550(3) 0.84990(2) 0.04348(9) Uani d 1 . .
Br Br2 0.61751(4) 0.03664(3) 0.63196(2) 0.04169(9) Uani d 1 . .
O O1 0.6947(2) 0.0875(2) 0.90019(14) 0.0332(4) Uani d 1 . .
O O2 0.8164(3) 0.6055(2) 0.30554(14) 0.0405(4) Uani d 1 . .
O O3 0.8603(3) 0.7832(2) 0.39910(15) 0.0416(4) Uani d 1 . .
H H3A 0.891(4) 0.846(3) 0.3317(11) 0.050 Uiso d 1 . .
N N1 0.3942(3) 0.1688(3) 0.87692(17) 0.0327(4) Uani d 1 . .
H H1A 0.355(4) 0.097(3) 0.9439(12) 0.039 Uiso d 1 . .
H H1B 0.312(3) 0.227(3) 0.8307(19) 0.039 Uiso d 1 . .
C C1 0.5730(3) 0.1757(3) 0.84327(18) 0.0252(4) Uani d 1 . .
C C2 0.6307(3) 0.3004(3) 0.72637(17) 0.0241(4) Uani d 1 . .
C C3 0.6625(3) 0.4624(3) 0.71657(19) 0.0265(4) Uani d 1 . .
C C4 0.7250(3) 0.5743(3) 0.61079(19) 0.0278(5) Uani d 1 . .
H H4A 0.748438 0.683825 0.606128 0.033 Uiso calc 1 . .
C C5 0.7527(3) 0.5239(3) 0.51214(18) 0.0264(5) Uani d 1 . .
C C6 0.7196(3) 0.3647(3) 0.51800(19) 0.0276(5) Uani d 1 . .
H H6A 0.737311 0.331352 0.449673 0.033 Uiso calc 1 . .
C C7 0.6603(3) 0.2545(3) 0.62524(19) 0.0256(4) Uani d 1 . .
C C8 0.8134(3) 0.6414(3) 0.3944(2) 0.0308(5) Uani d 1 . .
O O4 0.9365(13) 0.9719(9) 0.1879(11) 0.0313(15) Uani d 0.598(8) A 1
H H4B 1.0530(14) 0.964(8) 0.184(5) 0.047 Uiso d 0.598(8) A 1
C C9 0.872(3) 1.205(2) 0.2603(12) 0.060(2) Uani d 0.598(8) A 1
H H9A 0.820755 1.320374 0.241438 0.091 Uiso calc 0.598(8) A 1
H H9B 1.000209 1.198652 0.278449 0.091 Uiso calc 0.598(8) A 1
H H9C 0.796644 1.135893 0.327854 0.091 Uiso calc 0.598(8) A 1
C C10 0.8716(7) 1.1441(5) 0.1583(4) 0.0345(13) Uani d 0.598(8) A 1
H H10A 0.739971 1.152928 0.141246 0.041 Uiso calc 0.598(8) A 1
C C11 0.9845(12) 1.2460(14) 0.0493(7) 0.0429(18) Uani d 0.598(8) A 1
H H11A 0.979250 1.201108 -0.014763 0.064 Uiso calc 0.598(8) A 1
H H11B 1.113936 1.241251 0.064208 0.064 Uiso calc 0.598(8) A 1
H H11C 0.933135 1.361577 0.028151 0.064 Uiso calc 0.598(8) A 1
O O4' 0.978(2) 0.9791(14) 0.1997(18) 0.0313(15) Uani d 0.402(8) A 2
H H4C 1.049(8) 0.954(10) 0.146(5) 0.047 Uiso d 0.402(8) A 2
C C9' 0.883(5) 1.202(4) 0.2791(18) 0.060(2) Uani d 0.402(8) A 2
H H9D 0.887410 1.321374 0.265058 0.091 Uiso calc 0.402(8) A 2
H H9E 0.938938 1.140568 0.350651 0.091 Uiso calc 0.402(8) A 2
H H9F 0.753869 1.174455 0.287647 0.091 Uiso calc 0.402(8) A 2
C C10' 0.9900(11) 1.1550(7) 0.1784(5) 0.0304(17) Uani d 0.402(8) A 2
H H10B 1.123331 1.176385 0.174482 0.036 Uiso calc 0.402(8) A 2
C C11' 0.9228(19) 1.250(2) 0.0639(10) 0.0429(18) Uani d 0.402(8) A 2
H H11D 0.793361 1.227577 0.065230 0.064 Uiso calc 0.402(8) A 2
H H11E 1.000083 1.215842 0.001592 0.064 Uiso calc 0.402(8) A 2
H H11F 0.931011 1.369041 0.049729 0.064 Uiso calc 0.402(8) A 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'
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'
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_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C8 O3 H3A . . 110(2) ?
C1 N1 H1A . . 119.3(18) ?
C1 N1 H1B . . 121.2(18) ?
H1A N1 H1B . . 119(2) ?
O1 C1 N1 . . 124.32(19) ?
O1 C1 C2 . . 118.97(19) ?
N1 C1 C2 . . 116.71(19) ?
C3 C2 C7 . . 117.58(19) ?
C3 C2 C1 . . 121.60(19) ?
C7 C2 C1 . . 120.79(19) ?
C4 C3 C2 . . 121.8(2) ?
C4 C3 Br1 . . 118.38(17) ?
C2 C3 Br1 . . 119.85(16) ?
C5 C4 C3 . . 118.9(2) ?
C5 C4 H4A . . 120.5 ?
C3 C4 H4A . . 120.5 ?
C6 C5 C4 . . 121.02(19) ?
C6 C5 C8 . . 117.7(2) ?
C4 C5 C8 . . 121.3(2) ?
C5 C6 C7 . . 118.9(2) ?
C5 C6 H6A . . 120.6 ?
C7 C6 H6A . . 120.6 ?
C6 C7 C2 . . 121.8(2) ?
C6 C7 Br2 . . 118.33(17) ?
C2 C7 Br2 . . 119.82(15) ?
O2 C8 O3 . . 124.9(2) ?
O2 C8 C5 . . 122.0(2) ?
O3 C8 C5 . . 113.2(2) ?
C10 O4 H4B . . 109(5) ?
C10 C9 H9A . . 109.5 ?
C10 C9 H9B . . 109.5 ?
H9A C9 H9B . . 109.5 ?
C10 C9 H9C . . 109.5 ?
H9A C9 H9C . . 109.5 ?
H9B C9 H9C . . 109.5 ?
O4 C10 C9 . . 109.7(8) ?
O4 C10 C11 . . 110.9(7) ?
C9 C10 C11 . . 112.8(10) ?
O4 C10 H10A . . 107.8 ?
C9 C10 H10A . . 107.8 ?
C11 C10 H10A . . 107.8 ?
C10 C11 H11A . . 109.5 ?
C10 C11 H11B . . 109.5 ?
H11A C11 H11B . . 109.5 ?
C10 C11 H11C . . 109.5 ?
H11A C11 H11C . . 109.5 ?
H11B C11 H11C . . 109.5 ?
C10' O4' H4C . . 106(6) ?
C10' C9' H9D . . 109.5 ?
C10' C9' H9E . . 109.5 ?
H9D C9' H9E . . 109.5 ?
C10' C9' H9F . . 109.5 ?
H9D C9' H9F . . 109.5 ?
H9E C9' H9F . . 109.5 ?
O4' C10' C9' . . 108.5(13) ?
O4' C10' C11' . . 109.7(10) ?
C9' C10' C11' . . 113.5(14) ?
O4' C10' H10B . . 108.3 ?
C9' C10' H10B . . 108.3 ?
C11' C10' H10B . . 108.3 ?
C10' C11' H11D . . 109.5 ?
C10' C11' H11E . . 109.5 ?
H11D C11' H11E . . 109.5 ?
C10' C11' H11F . . 109.5 ?
H11D C11' H11F . . 109.5 ?
H11E C11' H11F . . 109.5 ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
Br1 C3 . 1.893(2) ?
Br2 C7 . 1.890(2) ?
O1 C1 . 1.236(3) ?
O2 C8 . 1.213(3) ?
O3 C8 . 1.311(3) ?
O3 H3A . 0.839(3) ?
N1 C1 . 1.311(3) ?
N1 H1A . 0.880(3) ?
N1 H1B . 0.880(3) ?
C1 C2 . 1.515(3) ?
C2 C3 . 1.389(3) ?
C2 C7 . 1.390(3) ?
C3 C4 . 1.385(3) ?
C4 C5 . 1.382(3) ?
C4 H4A . 0.9500 ?
C5 C6 . 1.381(3) ?
C5 C8 . 1.501(3) ?
C6 C7 . 1.385(3) ?
C6 H6A . 0.9500 ?
O4 C10 . 1.437(8) ?
O4 H4B . 0.840(3) ?
C9 C10 . 1.492(10) ?
C9 H9A . 0.9800 ?
C9 H9B . 0.9800 ?
C9 H9C . 0.9800 ?
C10 C11 . 1.517(8) ?
C10 H10A . 1.0000 ?
C11 H11A . 0.9800 ?
C11 H11B . 0.9800 ?
C11 H11C . 0.9800 ?
O4' C10' . 1.448(11) ?
O4' H4C . 0.840(3) ?
C9' C10' . 1.497(13) ?
C9' H9D . 0.9800 ?
C9' H9E . 0.9800 ?
C9' H9F . 0.9800 ?
C10' C11' . 1.492(12) ?
C10' H10B . 1.0000 ?
C11' H11D . 0.9800 ?
C11' H11E . 0.9800 ?
C11' H11F . 0.9800 ?
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
_geom_hbond_publ_flag
O3 H3A O4 . 0.839(3) 1.744(13) 2.580(12) 174(3) yes
O3 H3A O4' . 0.839(3) 1.724(19) 2.560(19) 173(3) yes
N1 H1A O1 2_657 0.880(3) 2.057(6) 2.929(2) 171(3) yes
N1 H1B O2 2_666 0.880(3) 2.075(9) 2.931(3) 164(3) yes
O4 H4B O1 2_766 0.840(3) 2.05(3) 2.802(11) 149(5) yes
O4' H4C O1 2_766 0.840(3) 1.90(5) 2.606(18) 141(7) yes
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_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
O1 C1 C2 C3 . . . . -91.0(3) ?
N1 C1 C2 C3 . . . . 89.3(3) ?
O1 C1 C2 C7 . . . . 86.7(3) ?
N1 C1 C2 C7 . . . . -93.0(3) ?
C7 C2 C3 C4 . . . . -1.3(3) ?
C1 C2 C3 C4 . . . . 176.4(2) ?
C7 C2 C3 Br1 . . . . 178.09(16) ?
C1 C2 C3 Br1 . . . . -4.2(3) ?
C2 C3 C4 C5 . . . . 1.3(3) ?
Br1 C3 C4 C5 . . . . -178.05(16) ?
C3 C4 C5 C6 . . . . -0.2(3) ?
C3 C4 C5 C8 . . . . 177.7(2) ?
C4 C5 C6 C7 . . . . -0.9(3) ?
C8 C5 C6 C7 . . . . -178.9(2) ?
C5 C6 C7 C2 . . . . 0.9(3) ?
C5 C6 C7 Br2 . . . . -179.53(16) ?
C3 C2 C7 C6 . . . . 0.1(3) ?
C1 C2 C7 C6 . . . . -177.6(2) ?
C3 C2 C7 Br2 . . . . -179.40(16) ?
C1 C2 C7 Br2 . . . . 2.8(3) ?
C6 C5 C8 O2 . . . . 7.2(3) ?
C4 C5 C8 O2 . . . . -170.8(2) ?
C6 C5 C8 O3 . . . . -173.2(2) ?
C4 C5 C8 O3 . . . . 8.9(3) ?

_cod_database_fobs_code 1561945
