#------------------------------------------------------------------------------
#$Date: 2016-02-13 13:50:18 +0100 (Sat 13 de Feb de 2016) $
#$Revision: 176428 $
#$URL: svn://www.crystallography.net/cod/cif/1/52/00/1520028.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_1520028
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 2ybc'
_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
_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                 92.866(5)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   16.189(2)
_cell_length_b                   4.6448(7)
_cell_length_c                   9.8821(17)
_cell_measurement_reflns_used    1957
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      30.51
_cell_measurement_theta_min      4.13
_cell_volume                     742.15(19)
_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 0.969
_diffrn_measured_fraction_theta_max 0.876
_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  0.0448
_diffrn_reflns_av_unetI/netI     0.0744
_diffrn_reflns_Laue_measured_fraction_full 0.969
_diffrn_reflns_Laue_measured_fraction_max 0.876
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_k_max       2
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_number            3504
_diffrn_reflns_point_group_measured_fraction_full 0.969
_diffrn_reflns_point_group_measured_fraction_max 0.876
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.536
_diffrn_reflns_theta_min         1.259
_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    5.463
_exptl_absorpt_correction_T_max  0.811
_exptl_absorpt_correction_T_min  0.624
_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    1.790
_exptl_crystal_description       plate
_exptl_crystal_F_000             392
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.04
_refine_diff_density_max         1.139
_refine_diff_density_min         -1.341
_refine_diff_density_rms         0.209
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.022
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     91
_refine_ls_number_reflns         1998
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.022
_refine_ls_R_factor_all          0.0660
_refine_ls_R_factor_gt           0.0524
_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)+(0.1000P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1469
_refine_ls_wR_factor_ref         0.1579
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1565
_reflns_number_total             1998
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            c5cy00627a2.cif
_cod_data_source_block           HG_SS16
_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_cell_volume        742.2(2)
_cod_original_sg_symbol_H-M      P2(1)/c
_cod_database_code               1520028
#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   0.342
_shelx_estimated_absorpt_t_max   0.811
_shelxl_version_number           2014-3
_shelx_res_file
;
TITL HG_SS16 in P2(1)/c
CELL 0.71073  16.1894   4.6448   9.8821  90.000  92.866  90.000
ZERR    4.00   0.0024   0.0007   0.0017   0.000   0.005   0.000
LATT 1
SYMM -X, 0.5+Y, 0.5-Z
SFAC C  H  N  Br O
UNIT 28 24 4 4 4
LIST 6 ! automatically inserted. Change 6 to 4 for CHECKCIF!!
L.S. 20
BOND
ACTA
CONF
FMAP 2
PLAN 5
SIZE 0.04 0.25 0.25
TEMP 23.000
WGHT    0.100000
FVAR       0.24121
MOLE 1
BR1   4    0.424131    0.702958    0.667735    11.00000    0.01416    0.03543 =
         0.02619   -0.00025   -0.00652    0.00037
N1    3    0.059748    0.782556    0.382123    11.00000    0.01738    0.03756 =
         0.00970   -0.00110   -0.00312    0.00400
AFIX  93
H1A   2    0.013267    0.871780    0.383872    11.00000   -1.20000
H1B   2    0.074511    0.704845    0.308126    11.00000   -1.20000
AFIX   0
O1    5    0.090589    0.873080    0.603679    11.00000    0.01782    0.03719 =
         0.00977   -0.00110   -0.00267    0.00400
C1    1    0.190113    0.612929    0.481690    11.00000    0.01408    0.02352 =
         0.01076    0.00340   -0.00245   -0.00052
C2    1    0.201417    0.397745    0.386317    11.00000    0.02175    0.02446 =
         0.01237    0.00168   -0.00254   -0.00167
AFIX  43
H2    2    0.157364    0.338679    0.328945    11.00000   -1.20000
AFIX   0
C3    1    0.279163    0.270854    0.377094    11.00000    0.02708    0.02494 =
         0.01782    0.00161   -0.00115    0.00104
AFIX  43
H3    2    0.286303    0.125530    0.314003    11.00000   -1.20000
AFIX   0
C4    1    0.345476    0.357863    0.460140    11.00000    0.02185    0.02464 =
         0.01999    0.00439    0.00209    0.00488
AFIX  43
H4    2    0.397251    0.274032    0.453091    11.00000   -1.20000
AFIX   0
C5    1    0.333304    0.573598    0.554653    11.00000    0.01989    0.02556 =
         0.01388    0.00609   -0.00114   -0.00218
C6    1    0.255806    0.701055    0.568183    11.00000    0.01617    0.02130 =
         0.01280    0.00037   -0.00225   -0.00186
AFIX  43
H6    2    0.248361    0.841531    0.633518    11.00000   -1.20000
AFIX   0
C7    1    0.108745    0.764770    0.493729    11.00000    0.01547    0.02541 =
         0.01072    0.00193   -0.00129   -0.00213
HKLF 4
REM  HG_SS16 in P2(1)/c
REM R1 =  0.0524 for    1565 Fo > 4sig(Fo)  and  0.0660 for all    1998 data
REM     91 parameters refined using      0 restraints
END
WGHT      0.1061      0.0000
REM Highest difference peak  1.139,  deepest hole -1.341,  1-sigma level  0.209
Q1    1   0.4783  0.6949  0.6926  11.00000  0.05    1.14
Q2    1   0.3717  0.6974  0.6404  11.00000  0.05    1.05
Q3    1   0.3790  0.6968  0.7925  11.00000  0.05    1.00
Q4    1   0.4826  0.2018  0.6363  11.00000  0.05    0.86
Q5    1   0.4692  0.6964  0.5446  11.00000  0.05    0.81
;
_shelx_res_checksum              32440
#END Tags that were not found in dictionaries
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
Br1 Br 0.42413(2) 0.70296(10) 0.66773(4) 0.02551(19) Uani 1 1 d . .
N1 N 0.0597(2) 0.7826(7) 0.3821(3) 0.0217(7) Uani 1 1 d . .
H1A H 0.0133 0.8718 0.3839 0.026 Uiso 1 1 calc R U
H1B H 0.0745 0.7048 0.3081 0.026 Uiso 1 1 calc R U
O1 O 0.09059(16) 0.8731(7) 0.6037(2) 0.0217(6) Uani 1 1 d . .
C1 C 0.1901(2) 0.6129(8) 0.4817(3) 0.0162(7) Uani 1 1 d . .
C2 C 0.2014(2) 0.3977(9) 0.3863(3) 0.0196(7) Uani 1 1 d . .
H2 H 0.1574 0.3387 0.3289 0.024 Uiso 1 1 calc R U
C3 C 0.2792(3) 0.2709(9) 0.3771(4) 0.0234(8) Uani 1 1 d . .
H3 H 0.2863 0.1255 0.3140 0.028 Uiso 1 1 calc R U
C4 C 0.3455(3) 0.3579(9) 0.4601(4) 0.0221(8) Uani 1 1 d . .
H4 H 0.3973 0.2740 0.4531 0.027 Uiso 1 1 calc R U
C5 C 0.3333(2) 0.5736(9) 0.5547(3) 0.0198(7) Uani 1 1 d . .
C6 C 0.2558(2) 0.7011(8) 0.5682(4) 0.0169(7) Uani 1 1 d . .
H6 H 0.2484 0.8415 0.6335 0.020 Uiso 1 1 calc R U
C7 C 0.1087(2) 0.7648(8) 0.4937(4) 0.0173(7) 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
Br1 0.0142(3) 0.0354(3) 0.0262(3) -0.00025(16) -0.00652(18) 0.00037(14)
N1 0.0174(17) 0.0376(19) 0.0097(12) -0.0011(12) -0.0031(13) 0.0040(13)
O1 0.0178(13) 0.0372(15) 0.0098(10) -0.0011(11) -0.0027(10) 0.0040(12)
C1 0.0141(16) 0.0235(16) 0.0108(13) 0.0034(13) -0.0025(12) -0.0005(14)
C2 0.0218(19) 0.0245(18) 0.0124(13) 0.0017(14) -0.0025(14) -0.0017(15)
C3 0.027(2) 0.0249(19) 0.0178(16) 0.0016(14) -0.0011(16) 0.0010(16)
C4 0.0218(19) 0.0246(18) 0.0200(16) 0.0044(15) 0.0021(15) 0.0049(15)
C5 0.0199(18) 0.0256(19) 0.0139(13) 0.0061(13) -0.0011(14) -0.0022(14)
C6 0.0162(18) 0.0213(17) 0.0128(14) 0.0004(13) -0.0022(14) -0.0019(13)
C7 0.0155(18) 0.0254(18) 0.0107(14) 0.0019(13) -0.0013(14) -0.0021(14)
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'
Br Br -0.2901 2.4595 '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
C2 C1 C6 120.3(3)
C2 C1 C7 122.4(3)
C6 C1 C7 117.3(3)
C1 C2 C3 119.8(4)
C4 C3 C2 121.0(4)
C3 C4 C5 118.6(4)
C4 C5 C6 121.8(4)
C4 C5 Br1 119.4(3)
C6 C5 Br1 118.8(3)
C1 C6 C5 118.5(3)
O1 C7 N1 122.8(4)
O1 C7 C1 120.3(3)
N1 C7 C1 116.9(3)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
Br1 C5 1.899(4)
N1 C7 1.329(5)
O1 C7 1.246(4)
C1 C2 1.392(5)
C1 C6 1.392(5)
C1 C7 1.504(5)
C2 C3 1.397(6)
C3 C4 1.379(6)
C4 C5 1.391(5)
C5 C6 1.400(5)
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
C6 C1 C2 C3 -0.3(5)
C7 C1 C2 C3 178.0(3)
C1 C2 C3 C4 -0.8(6)
C2 C3 C4 C5 0.6(6)
C3 C4 C5 C6 0.7(5)
C3 C4 C5 Br1 -178.7(3)
C2 C1 C6 C5 1.5(5)
C7 C1 C6 C5 -176.8(3)
C4 C5 C6 C1 -1.7(5)
Br1 C5 C6 C1 177.7(3)
C2 C1 C7 O1 153.9(3)
C6 C1 C7 O1 -27.8(5)
C2 C1 C7 N1 -27.8(5)
C6 C1 C7 N1 150.5(3)
