#------------------------------------------------------------------------------
#$Date: 2015-09-05 22:46:15 +0200 (Sat 05 de Sep de 2015) $
#$Revision: 154564 $
#$URL: svn://www.crystallography.net/cod/cif/4/51/33/4513344.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_4513344
loop_
_publ_author_name
'López-Mejías, Vilmalí'
'Matzger, Adam J.'
_publ_section_title
;
 Structure--Polymorphism Study of Fenamates: Toward Developing an
 Understanding of the Polymorphophore
;
_journal_issue                   8
_journal_name_full               'Crystal Growth & Design'
_journal_page_first              3955
_journal_paper_doi               10.1021/acs.cgd.5b00570
_journal_volume                  15
_journal_year                    2015
_chemical_formula_moiety         'C13 H10 Br N O2'
_chemical_formula_sum            'C13 H10 Br N O2'
_chemical_formula_weight         292.13
_chemical_name_systematic
;
 ?
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.577(6)
_cell_angle_beta                 91.090(6)
_cell_angle_gamma                98.171(7)
_cell_formula_units_Z            2
_cell_length_a                   3.8698(1)
_cell_length_b                   11.1898(5)
_cell_length_c                   13.2866(9)
_cell_measurement_reflns_used    3762
_cell_measurement_temperature    85(2)
_cell_measurement_theta_max      68.30
_cell_measurement_theta_min      3.30
_cell_volume                     569.35(5)
_computing_cell_refinement       'CrystalClear-SM Expert 2.0 r5'
_computing_data_collection
'CrystalClear-SM Expert 2.0 r5 (Rigaku, 2010)'
_computing_data_reduction        'CrystalClear-SM Expert 2.0 r5'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      85(2)
_diffrn_detector_area_resol_mean 14.629
_diffrn_measured_fraction_theta_full 0.963
_diffrn_measured_fraction_theta_max 0.963
_diffrn_measurement_device_type  'Rigaku Saturn744+ CCD'
_diffrn_measurement_method       ω
_diffrn_radiation_monochromator  confocal
_diffrn_radiation_source         'rotating anode'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54187
_diffrn_reflns_av_R_equivalents  0.1908
_diffrn_reflns_av_sigmaI/netI    0.1690
_diffrn_reflns_limit_h_max       4
_diffrn_reflns_limit_h_min       -4
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            9224
_diffrn_reflns_theta_full        68.22
_diffrn_reflns_theta_max         68.22
_diffrn_reflns_theta_min         3.99
_exptl_absorpt_coefficient_mu    4.832
_exptl_absorpt_correction_T_max  0.9952
_exptl_absorpt_correction_T_min  0.7603
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Jacobson, R. (1998) Private communication'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.704
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             292
_exptl_crystal_size_max          0.06
_exptl_crystal_size_mid          0.04
_exptl_crystal_size_min          0.001
_refine_diff_density_max         1.516
_refine_diff_density_min         -1.477
_refine_diff_density_rms         0.213
_refine_ls_extinction_coef       0.0194(13)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   0.995
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     162
_refine_ls_number_reflns         2016
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      0.994
_refine_ls_R_factor_all          0.1432
_refine_ls_R_factor_gt           0.1177
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.1834P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2744
_refine_ls_wR_factor_ref         0.3094
_reflns_number_gt                1205
_reflns_number_total             2016
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            cg5b00570_si_002.cif
_cod_data_source_block           TAanalogue4-formI
_cod_depositor_comments
'Adding full bibliography for 4513336--4513344.cif.'
_cod_database_code               4513344
loop_
_symmetry_equiv_pos_as_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
Br1 Br -0.00324(10) 1.17065(4) 0.42265(3) 0.05943(15) Uani 1 1 d .
N1 N 0.0275(9) 0.7958(3) 0.1803(2) 0.0532(10) Uani 1 1 d D
H1A H -0.020(9) 0.7639(19) 0.1187(8) 0.064 Uiso 1 1 d D
O1 O -0.2926(7) 0.6218(3) 0.05798(17) 0.0542(8) Uani 1 1 d .
O2 O -0.3689(8) 0.4332(2) 0.11442(17) 0.0535(8) Uani 1 1 d D
H2 H -0.413(10) 0.3913(14) 0.0623(8) 0.067(13) Uiso 1 1 d D
C1 C -0.2476(10) 0.5472(4) 0.1248(3) 0.0504(11) Uani 1 1 d .
C2 C -0.0583(10) 0.5802(4) 0.2220(3) 0.0472(11) Uani 1 1 d .
C3 C -0.0105(9) 0.4911(3) 0.2872(2) 0.0425(10) Uani 1 1 d .
H3A H -0.1022 0.4099 0.2704 0.051 Uiso 1 1 calc R
C4 C 0.1689(10) 0.5163(4) 0.3773(3) 0.0496(11) Uani 1 1 d .
H4A H 0.2050 0.4530 0.4216 0.059 Uiso 1 1 calc R
C5 C 0.2941(10) 0.6334(4) 0.4020(3) 0.0538(12) Uani 1 1 d .
H5A H 0.4073 0.6521 0.4654 0.065 Uiso 1 1 calc R
C6 C 0.2571(11) 0.7249(4) 0.3352(3) 0.0554(13) Uani 1 1 d .
H6A H 0.3613 0.8050 0.3512 0.066 Uiso 1 1 calc R
C7 C 0.0727(11) 0.7021(4) 0.2462(3) 0.0510(12) Uani 1 1 d .
C8 C 0.0990(10) 0.9188(4) 0.1983(3) 0.0525(12) Uani 1 1 d .
C9 C 0.0363(10) 0.9757(4) 0.2886(3) 0.0471(11) Uani 1 1 d .
H9A H -0.0553 0.9292 0.3439 0.056 Uiso 1 1 calc R
C10 C 0.1064(11) 1.0978(4) 0.2972(3) 0.0569(13) Uani 1 1 d .
C11 C 0.2453(11) 1.1718(4) 0.2218(3) 0.0563(13) Uani 1 1 d .
H11A H 0.2916 1.2571 0.2300 0.068 Uiso 1 1 calc R
C12 C 0.3138(11) 1.1143(4) 0.1328(3) 0.0571(12) Uani 1 1 d .
H12A H 0.4163 1.1618 0.0794 0.069 Uiso 1 1 calc R
C13 C 0.2412(11) 0.9944(4) 0.1191(3) 0.0530(12) Uani 1 1 d .
H13A H 0.2851 0.9594 0.0560 0.064 Uiso 1 1 calc R
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
Br1 0.0590(3) 0.0689(3) 0.0491(2) -0.0129(2) 0.0057(2) 0.0048(2)
N1 0.0637(19) 0.051(2) 0.0417(15) -0.0014(15) 0.0090(14) -0.0026(17)
O1 0.0736(17) 0.0535(16) 0.0313(11) -0.0035(12) -0.0027(11) -0.0050(15)
O2 0.0710(17) 0.0470(15) 0.0378(11) -0.0102(12) -0.0026(12) -0.0068(14)
C1 0.053(2) 0.061(2) 0.0346(16) -0.0092(17) -0.0006(15) 0.0008(19)
C2 0.056(2) 0.047(2) 0.0366(16) -0.0073(16) 0.0068(15) -0.0010(18)
C3 0.0457(18) 0.040(2) 0.0388(16) -0.0042(16) 0.0092(14) -0.0046(17)
C4 0.055(2) 0.053(2) 0.0418(17) 0.0000(17) 0.0056(16) 0.0119(18)
C5 0.050(2) 0.073(3) 0.0399(18) -0.0062(19) -0.0035(16) 0.012(2)
C6 0.058(2) 0.057(3) 0.0470(19) -0.001(2) -0.0011(17) -0.004(2)
C7 0.056(2) 0.060(3) 0.0339(16) 0.0042(17) 0.0043(15) -0.001(2)
C8 0.0478(19) 0.062(3) 0.0443(18) -0.0042(18) 0.0094(15) -0.0035(19)
C9 0.0503(19) 0.049(2) 0.0386(16) -0.0046(17) 0.0115(14) -0.0043(18)
C10 0.051(2) 0.065(3) 0.054(2) -0.002(2) 0.0085(17) 0.007(2)
C11 0.065(2) 0.052(2) 0.051(2) 0.0020(19) 0.0040(18) 0.007(2)
C12 0.056(2) 0.063(3) 0.0486(19) -0.0118(19) 0.0133(16) -0.004(2)
C13 0.061(2) 0.057(3) 0.0388(17) -0.0108(18) 0.0109(16) 0.001(2)
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.6763 1.2805 '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
C8 N1 C7 128.1(3)
O1 C1 O2 121.7(3)
O1 C1 C2 123.7(4)
O2 C1 C2 114.6(3)
C3 C2 C7 120.3(3)
C3 C2 C1 118.8(4)
C7 C2 C1 120.9(4)
C2 C3 C4 121.1(4)
C5 C4 C3 119.2(4)
C4 C5 C6 120.3(4)
C7 C6 C5 121.2(4)
C6 C7 N1 120.9(4)
C6 C7 C2 117.6(4)
N1 C7 C2 121.5(3)
N1 C8 C9 124.7(3)
N1 C8 C13 118.4(3)
C9 C8 C13 116.9(4)
C10 C9 C8 119.8(4)
C9 C10 C11 124.0(4)
C9 C10 Br1 117.5(3)
C11 C10 Br1 118.5(3)
C10 C11 C12 115.8(4)
C13 C12 C11 122.8(4)
C12 C13 C8 120.6(4)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
Br1 C10 1.929(4)
N1 C8 1.383(6)
N1 C7 1.401(5)
O1 C1 1.251(5)
O2 C1 1.300(5)
C1 C2 1.490(5)
C2 C3 1.357(5)
C2 C7 1.417(6)
C3 C4 1.379(5)
C4 C5 1.365(6)
C5 C6 1.383(6)
C6 C7 1.372(5)
C8 C9 1.393(5)
C8 C13 1.426(5)
C9 C10 1.358(6)
C10 C11 1.375(6)
C11 C12 1.388(6)
C12 C13 1.341(6)
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N1 H1A O1 0.894(12) 1.94(2) 2.672(4) 138.1(19) .
O2 H2 O1 0.834(12) 1.94(2) 2.640(3) 141(3) 2_465
