#------------------------------------------------------------------------------
#$Date: 2017-10-13 01:32:00 +0200 (vie 13 de oct de 2017) $
#$Revision: 201954 $
#$URL: svn://www.crystallography.net/cod/cif/1/50/43/1504322.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_1504322
loop_
_publ_author_name
'Hursthouse, Michael B.'
'Huth, L. Susanne'
'Threlfall, Terence L.'
_publ_section_title
;
 Why Do Organic Compounds Crystallise Well or Badly or Ever so Slowly? Why
 Is Crystallisation Nevertheless Such a Good Purification
 Technique?†
;
_journal_issue                   6
_journal_name_full               'Organic Process Research & Development'
_journal_page_first              1231
_journal_paper_doi               10.1021/op900169b
_journal_volume                  13
_journal_year                    2009
_chemical_formula_moiety         'C7 H6 Br N O'
_chemical_formula_sum            'C7 H6 Br N O'
_chemical_formula_weight         200.04
_chemical_name_common            meta-Bromoformanilide
_chemical_name_systematic
;
 ?
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 93.952(6)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   9.1595(8)
_cell_length_b                   11.8459(10)
_cell_length_c                   6.6063(5)
_cell_measurement_reflns_used    26477
_cell_measurement_temperature    120(2)
_cell_measurement_theta_max      27.48
_cell_measurement_theta_min      2.91
_cell_volume                     715.10(10)
_computing_cell_refinement
'DENZO (Otwinowski & Minor, 1997) & COLLECT (Hooft, R.W.W., 1998)'
_computing_data_collection       'COLLECT (Hooft, R.W.W., 1998)'
_computing_data_reduction
'DENZO (Otwinowski & Minor, 1997) & COLLECT (Hooft, R.W.W., 1998)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      120(2)
_diffrn_detector_area_resol_mean 9.091
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_device_type
'Bruker-Nonius Roper CCD camera on κ-goniostat'
_diffrn_measurement_method       'φ & ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'Bruker-Nonius FR591 rotating anode'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0590
_diffrn_reflns_av_sigmaI/netI    0.0428
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       7
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_number            9195
_diffrn_reflns_theta_full        27.48
_diffrn_reflns_theta_max         27.48
_diffrn_reflns_theta_min         3.54
_exptl_absorpt_coefficient_mu    5.670
_exptl_absorpt_correction_T_max  0.3968
_exptl_absorpt_correction_T_min  0.1221
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS 2007/2 (Sheldrick, G.M., 2007)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.858
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       'cut fragment'
_exptl_crystal_F_000             392
_exptl_crystal_size_max          0.64
_exptl_crystal_size_mid          0.60
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.725
_refine_diff_density_min         -0.880
_refine_diff_density_rms         0.123
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.066
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     95
_refine_ls_number_reflns         1632
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.066
_refine_ls_R_factor_all          0.0476
_refine_ls_R_factor_gt           0.0401
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0589P)²+0.3682P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0982
_refine_ls_wR_factor_ref         0.1023
_reflns_number_gt                1418
_reflns_number_total             1632
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            op900169b_si_001.cif
_cod_data_source_block           2008lsh146
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to /home/saulius/struct/CIF-dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_original_sg_symbol_H-M      P2(1)/c
_cod_database_code               1504322
loop_
_symmetry_equiv_pos_as_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
C1 C 0.6856(3) 0.4963(2) 0.6189(5) 0.0253(6) Uani 1 1 d .
C2 C 0.7775(3) 0.4221(2) 0.5230(5) 0.0275(6) Uani 1 1 d .
H2 H 0.7978 0.3490 0.5768 0.033 Uiso 1 1 calc R
C3 C 0.8380(3) 0.4578(2) 0.3480(5) 0.0287(6) Uani 1 1 d .
C4 C 0.8158(4) 0.5654(3) 0.2691(5) 0.0328(7) Uani 1 1 d .
H4 H 0.8615 0.5885 0.1511 0.039 Uiso 1 1 calc R
C5 C 0.7254(4) 0.6381(2) 0.3662(5) 0.0334(7) Uani 1 1 d .
H5 H 0.7090 0.7122 0.3148 0.040 Uiso 1 1 calc R
C6 C 0.6586(3) 0.6037(2) 0.5378(5) 0.0286(6) Uani 1 1 d .
H6 H 0.5942 0.6535 0.6006 0.034 Uiso 1 1 calc R
C7 C 0.6098(4) 0.3657(2) 0.8823(5) 0.0290(7) Uani 1 1 d .
H7 H 0.6552 0.3040 0.8195 0.035 Uiso 1 1 calc R
N1 N 0.6192(3) 0.4685(2) 0.7984(4) 0.0274(5) Uani 1 1 d D
H1N H 0.571(4) 0.522(3) 0.854(6) 0.041(10) Uiso 1 1 d D
O1 O 0.5457(3) 0.34754(16) 1.0355(4) 0.0325(5) Uani 1 1 d .
Br1 Br 0.95889(3) 0.35478(3) 0.21539(5) 0.03577(17) Uani 1 1 d .
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
C1 0.0271(15) 0.0178(13) 0.0310(15) -0.0013(10) 0.0023(12) -0.0032(11)
C2 0.0321(16) 0.0172(12) 0.0337(15) -0.0007(11) 0.0049(13) -0.0009(11)
C3 0.0305(15) 0.0234(14) 0.0321(15) -0.0050(11) 0.0021(12) -0.0030(11)
C4 0.0395(18) 0.0288(15) 0.0306(16) 0.0030(12) 0.0053(13) -0.0051(13)
C5 0.0386(18) 0.0204(14) 0.0405(19) 0.0063(11) -0.0009(15) -0.0011(12)
C6 0.0299(15) 0.0193(13) 0.0366(16) -0.0012(11) 0.0024(13) -0.0003(12)
C7 0.0335(17) 0.0196(13) 0.0345(16) -0.0022(11) 0.0057(13) 0.0003(11)
N1 0.0336(14) 0.0180(11) 0.0315(13) 0.0000(9) 0.0076(11) 0.0020(10)
O1 0.0399(13) 0.0234(11) 0.0351(13) 0.0021(8) 0.0102(10) -0.0003(8)
Br1 0.0364(2) 0.0301(2) 0.0424(2) -0.00793(12) 0.01428(16) -0.00442(12)
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
C6 C1 C2 119.7(3)
C6 C1 N1 117.4(3)
C2 C1 N1 122.9(2)
C3 C2 C1 118.4(3)
C3 C2 H2 120.8
C1 C2 H2 120.8
C2 C3 C4 122.6(3)
C2 C3 Br1 117.9(2)
C4 C3 Br1 119.5(2)
C5 C4 C3 118.4(3)
C5 C4 H4 120.8
C3 C4 H4 120.8
C4 C5 C6 120.6(3)
C4 C5 H5 119.7
C6 C5 H5 119.7
C5 C6 C1 120.3(3)
C5 C6 H6 119.8
C1 C6 H6 119.8
O1 C7 N1 123.3(3)
O1 C7 H7 118.4
N1 C7 H7 118.4
C7 N1 C1 127.1(3)
C7 N1 H1N 116(3)
C1 N1 H1N 116(3)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C1 C6 1.396(4)
C1 C2 1.398(4)
C1 N1 1.408(4)
C2 C3 1.383(4)
C2 H2 0.9500
C3 C4 1.386(4)
C3 Br1 1.902(3)
C4 C5 1.382(5)
C4 H4 0.9500
C5 C6 1.386(5)
C5 H5 0.9500
C6 H6 0.9500
C7 O1 1.224(4)
C7 N1 1.344(4)
C7 H7 0.9500
N1 H1N 0.874(18)
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 H1N O1 0.874(18) 2.037(19) 2.909(3) 176(4) 3_667
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 13249736
