#------------------------------------------------------------------------------
#$Date: 2016-02-13 13:50:18 +0100 (Sat 13 de Feb de 2016) $
#$Revision: 176428 $
#$URL: svn://www.crystallography.net/cod/cif/1/52/00/1520029.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_1520029
loop_
_publ_author_name
'Gulyás, Henrik'
'Rivilla, Ivan'
'Curreli, Simona'
'Freixa, Zoraida'
'van Leeuwen, Piet W. N. M.'
_publ_section_title
;
 Highly active, chemo- and enantioselective Pt-SPO catalytic systems for
 the synthesis of aromatic carboxamides
;
_journal_issue                   7
_journal_name_full               'Catal. Sci. Technol.'
_journal_page_first              3822
_journal_paper_doi               10.1039/C5CY00627A
_journal_volume                  5
_journal_year                    2015
_chemical_formula_sum            'C7 H6 Br N O'
_chemical_formula_weight         200.04
_chemical_name_systematic
;
 ?
;
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_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
_audit_creation_method           SHELXL-2014
_audit_update_record
;
2015-04-27 deposited with the CCDC.
2015-05-26 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 93.465(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   5.0263(6)
_cell_length_b                   10.9683(15)
_cell_length_c                   13.3113(14)
_cell_measurement_reflns_used    707
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      31.17
_cell_measurement_theta_min      4.02
_cell_volume                     732.51(15)
_computing_cell_refinement       'Bruker APEX2 v2011.4-0'
_computing_data_collection       'Bruker APEX2 v2011.4-0'
_computing_data_reduction        'Bruker SAINT V7.60A'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'
_computing_structure_solution    Sir2011
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean 512
_diffrn_detector_type            '4K CCD area detector APEX II'
_diffrn_measured_fraction_theta_full 0.961
_diffrn_measured_fraction_theta_max 0.556
_diffrn_measurement_device_type  'Kappa 4-axis goniometer bruker-nonius'
_diffrn_measurement_method
;
 Fullsphere data collection, phi and omega scans
;
_diffrn_measurement_specimen_support 'magnetic support with MicroMount'
_diffrn_radiation_monochromator  'Multilayer Montel 200 mirrors'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0073
_diffrn_reflns_av_unetI/netI     0.0128
_diffrn_reflns_Laue_measured_fraction_full 0.961
_diffrn_reflns_Laue_measured_fraction_max 0.556
_diffrn_reflns_limit_h_max       2
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -4
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            1110
_diffrn_reflns_point_group_measured_fraction_full 0.961
_diffrn_reflns_point_group_measured_fraction_max 0.556
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         31.971
_diffrn_reflns_theta_min         2.408
_diffrn_source                   'Rotating anode X-ray tube'
_diffrn_source_current           70
_diffrn_source_power             50
_diffrn_source_size              '0.3 mm x 0.3 mm fine focus'
_diffrn_source_type              'Bruker-Nonius FR 591'
_exptl_absorpt_coefficient_mu    5.535
_exptl_absorpt_correction_T_max  0.769
_exptl_absorpt_correction_T_min  0.626
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details
; 
 SADABS Version 2008/1 Bruker-Nonius
 Blessing, Acta Cryst. (1995) A51 33-38
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.814
_exptl_crystal_description       needle
_exptl_crystal_F_000             392
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.247
_refine_diff_density_min         -0.214
_refine_diff_density_rms         0.051
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.084
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     91
_refine_ls_number_reflns         980
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.084
_refine_ls_R_factor_all          0.0227
_refine_ls_R_factor_gt           0.0197
_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)+(0.0271P)²+0.5327P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0499
_refine_ls_wR_factor_ref         0.0512
_reflns_Friedel_coverage         0.000
_reflns_number_gt                903
_reflns_number_total             980
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            c5cy00627a2.cif
_cod_data_source_block           HG_SS20_0m
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to
/usr/data/users/saulius/crontab/automatic-downloads/rss-feeds/RSC/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 3271 2015-04-21 07:52:19Z andrius 

 Adding full bibliography for 1520028--1520034.cif.
;
_cod_original_sg_symbol_H-M      P2(1)/n
_cod_database_code               1520029
#BEGIN Tags that were not found in dictionaries:
_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   0.248
_shelx_estimated_absorpt_t_max   0.769
_shelxl_version_number           2014-3
_shelx_res_file
;
TITL HG_SS20_0m in P2(1)/n
CELL 0.71073   5.0263  10.9683  13.3113  90.000  93.465  90.000
ZERR    4.00   0.0006   0.0015   0.0014   0.000   0.003   0.000
LATT 1
SYMM 0.5-X, 0.5+Y, 0.5-Z
SFAC C  H  N  O  Br
UNIT 28 24 4 4 4
LIST 6 ! automatically inserted. Change 6 to 4 for CHECKCIF!!
L.S. 20
BOND
FMAP 2
ACTA
CONF
PLAN 5
SIZE 0.05 0.05 0.35
TEMP 23.000
WGHT    0.027100    0.532700
FVAR       0.24558
MOLE 1
BR1   5    0.154224   -0.053992    0.185861    11.00000    0.01780    0.02206 =
         0.02345   -0.00398    0.00060   -0.00286
N1    3    0.750781    0.060924    0.413444    11.00000    0.00881    0.03045 =
         0.01627    0.00084    0.00276    0.00155
AFIX  93
H1A   2    0.746138    0.037504    0.474970    11.00000   -1.20000
H1B   2    0.901494    0.071775    0.387433    11.00000   -1.20000
AFIX   0
O1    4    0.303447    0.065756    0.393216    11.00000    0.01004    0.03151 =
         0.01501    0.00267    0.00497    0.00040
C1    1    0.523930    0.080443    0.358286    11.00000    0.01150    0.01779 =
         0.01985   -0.00217    0.00002   -0.00002
C2    1    0.552100    0.123498    0.253130    11.00000    0.01246    0.01190 =
         0.01815   -0.00213    0.00477    0.00421
C3    1    0.394717    0.077763    0.170570    11.00000    0.01442    0.01680 =
         0.01890    0.00098    0.00373    0.00300
C4    1    0.420512    0.122698    0.074272    11.00000    0.02603    0.02121 =
         0.01697    0.00386    0.00630    0.00649
AFIX  43
H4    2    0.310192    0.094046    0.020815    11.00000   -1.20000
AFIX   0
C5    1    0.610299    0.209960    0.058189    11.00000    0.03332    0.02468 =
         0.02053    0.00980    0.01305    0.01199
AFIX  43
H5    2    0.629933    0.239207   -0.006522    11.00000   -1.20000
AFIX   0
C6    1    0.773607    0.254840    0.138544    11.00000    0.02416    0.01439 =
         0.03695    0.00734    0.01395    0.00346
AFIX  43
H6    2    0.901180    0.314048    0.127707    11.00000   -1.20000
AFIX   0
C7    1    0.743370    0.210283    0.234145    11.00000    0.01629    0.01113 =
         0.02708   -0.00003    0.00736    0.00215
AFIX  43
H7    2    0.854311    0.239252    0.287303    11.00000   -1.20000
AFIX   0
HKLF 4
REM  HG_SS20_0m in P2(1)/n
REM R1 =  0.0197 for     903 Fo > 4sig(Fo)  and  0.0227 for all     980 data
REM     91 parameters refined using      0 restraints
END
WGHT      0.0271      0.5327
REM Highest difference peak  0.247,  deepest hole -0.214,  1-sigma level  0.051
Q1    1   0.4669  0.1085  0.2158  11.00000  0.05    0.25
Q2    1   0.1052 -0.0543  0.2598  11.00000  0.05    0.23
Q3    1   0.6585  0.0467  0.3822  11.00000  0.05    0.23
Q4    1   0.5355  0.0899  0.2924  11.00000  0.05    0.23
Q5    1   0.6428  0.1746  0.2246  11.00000  0.05    0.19
;
_shelx_res_checksum              71363
#END Tags that were not found in dictionaries
loop_
_space_group_symop_operation_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_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
Br1 Br 0.15422(4) -0.05399(3) 0.18586(2) 0.02113(13) Uani 1 1 d . .
N1 N 0.7508(4) 0.0609(2) 0.41344(17) 0.0184(7) Uani 1 1 d . .
H1A H 0.7461 0.0375 0.4750 0.022 Uiso 1 1 calc R U
H1B H 0.9015 0.0718 0.3874 0.022 Uiso 1 1 calc R U
O1 O 0.3034(3) 0.06576(19) 0.39322(14) 0.0187(6) Uani 1 1 d . .
C1 C 0.5239(4) 0.0804(3) 0.3583(2) 0.0164(8) Uani 1 1 d . .
C2 C 0.5521(4) 0.1235(3) 0.2531(2) 0.0140(8) Uani 1 1 d . .
C3 C 0.3947(4) 0.0778(3) 0.1706(2) 0.0166(8) Uani 1 1 d . .
C4 C 0.4205(5) 0.1227(3) 0.0743(2) 0.0212(9) Uani 1 1 d . .
H4 H 0.3102 0.0940 0.0208 0.025 Uiso 1 1 calc R U
C5 C 0.6103(5) 0.2100(4) 0.0582(2) 0.0257(10) Uani 1 1 d . .
H5 H 0.6299 0.2392 -0.0065 0.031 Uiso 1 1 calc R U
C6 C 0.7736(5) 0.2548(3) 0.1385(2) 0.0247(9) Uani 1 1 d . .
H6 H 0.9012 0.3140 0.1277 0.030 Uiso 1 1 calc R U
C7 C 0.7434(4) 0.2103(3) 0.2341(2) 0.0179(8) Uani 1 1 d . .
H7 H 0.8543 0.2393 0.2873 0.022 Uiso 1 1 calc R U
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 0.01780(12) 0.0221(3) 0.0235(2) -0.00398(13) 0.00060(13) -0.00286(10)
N1 0.0088(7) 0.030(2) 0.0163(12) 0.0008(11) 0.0028(9) 0.0016(8)
O1 0.0100(6) 0.0315(17) 0.0150(10) 0.0027(9) 0.0050(8) 0.0004(7)
C1 0.0115(8) 0.018(2) 0.0198(15) -0.0022(12) 0.0000(11) 0.0000(9)
C2 0.0125(9) 0.012(2) 0.0182(14) -0.0021(13) 0.0048(11) 0.0042(9)
C3 0.0144(9) 0.017(2) 0.0189(15) 0.0010(13) 0.0037(11) 0.0030(9)
C4 0.0260(11) 0.021(3) 0.0170(15) 0.0039(15) 0.0063(13) 0.0065(12)
C5 0.0333(13) 0.025(3) 0.0205(16) 0.0098(16) 0.0131(14) 0.0120(13)
C6 0.0242(11) 0.014(3) 0.0369(18) 0.0073(16) 0.0140(14) 0.0035(11)
C7 0.0163(9) 0.011(2) 0.0271(16) 0.0000(14) 0.0074(12) 0.0022(10)
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
O1 C1 N1 121.8(3)
O1 C1 C2 122.10(18)
N1 C1 C2 116.1(2)
C7 C2 C3 117.7(3)
C7 C2 C1 119.6(2)
C3 C2 C1 122.6(2)
C4 C3 C2 121.0(3)
C4 C3 Br1 117.7(2)
C2 C3 Br1 121.2(2)
C5 C4 C3 119.7(2)
C4 C5 C6 120.4(3)
C7 C6 C5 119.2(3)
C6 C7 C2 121.8(2)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
Br1 C3 1.903(3)
N1 C1 1.336(2)
O1 C1 1.238(3)
C1 C2 1.492(4)
C2 C7 1.387(4)
C2 C3 1.407(3)
C3 C4 1.387(4)
C4 C5 1.377(5)
C5 C6 1.398(4)
C6 C7 1.380(4)
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
O1 C1 C2 C7 137.3(3)
N1 C1 C2 C7 -41.4(4)
O1 C1 C2 C3 -44.0(4)
N1 C1 C2 C3 137.3(3)
C7 C2 C3 C4 -3.3(4)
C1 C2 C3 C4 177.9(3)
C7 C2 C3 Br1 173.0(2)
C1 C2 C3 Br1 -5.7(4)
C2 C3 C4 C5 2.7(4)
Br1 C3 C4 C5 -173.8(2)
C3 C4 C5 C6 -1.1(5)
C4 C5 C6 C7 0.3(5)
C5 C6 C7 C2 -1.1(5)
C3 C2 C7 C6 2.6(4)
C1 C2 C7 C6 -178.7(3)
