#------------------------------------------------------------------------------
#$Date: 2016-02-13 13:50:18 +0100 (Sat 13 de Feb de 2016) $
#$Revision: 176428 $
#$URL: svn://www.crystallography.net/cod/cif/1/51/95/1519526.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_1519526
loop_
_publ_author_name
'Butts, Craig'
'Horton, Peter N.'
'Hursthouse, Michael B.'
_publ_section_title
;
 C12H19BrN2O
;
_journal_name_full               'Crystal Structure Report Archive'
_journal_page_first              946
_journal_year                    2002
_chemical_formula_sum            'C12 H19 Br N2 O'
_chemical_formula_weight         287.20
_space_group_IT_number           14
_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
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                90.00
_cell_angle_beta                 90.676(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   5.1010(2)
_cell_length_b                   18.7081(8)
_cell_length_c                   13.7459(7)
_cell_measurement_reflns_used    25197
_cell_measurement_temperature    120(2)
_cell_measurement_theta_max      23.24
_cell_measurement_theta_min      5.11
_cell_volume                     1311.68(10)
_computing_cell_refinement
' DENZO (Otwinowski & Minor, 1997) and COLLECT (Hooft, 1998)'
_computing_data_reduction
' DENZO (Otwinowski & Minor, 1997) and COLLECT (Hooft, 1998)'
_computing_molecular_graphics    'PLATON (Spek, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997b)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997a)'
_diffrn_ambient_temperature      120(2)
_diffrn_detector_area_resol_mean 9.091
_diffrn_measured_fraction_theta_full 0.990
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measurement_device_type  'Nonius KappaCCD Area Detector'
_diffrn_measurement_method       'φ and ω scans to fill Ewald Sphere'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'Nonius FR591 rotating anode'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0697
_diffrn_reflns_av_sigmaI/netI    0.0549
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            7915
_diffrn_reflns_theta_full        25.02
_diffrn_reflns_theta_max         25.02
_diffrn_reflns_theta_min         2.96
_exptl_absorpt_coefficient_mu    3.117
_exptl_absorpt_correction_T_max  0.5745
_exptl_absorpt_correction_T_min  0.5745
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SORTAV Blessing (1997)'
_exptl_crystal_colour            Colourless
_exptl_crystal_density_diffrn    1.454
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Block
_exptl_crystal_F_000             592
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.632
_refine_diff_density_min         -0.796
_refine_diff_density_rms         0.095
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.060
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     221
_refine_ls_number_reflns         2291
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.060
_refine_ls_R_factor_all          0.0527
_refine_ls_R_factor_gt           0.0387
_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)+(0.0529P)²+0.3265P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0920
_refine_ls_wR_factor_ref         0.0998
_reflns_number_gt                1857
_reflns_number_total             2291
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            eCrystal-946.cif
_cod_data_source_block           s92
_cod_depositor_comments
;
Citation :
Butts, Craig and Horton, Peter N. and Hursthouse, Michael B. (2002) 
University of Southampton, Crystal Structure Report Archive. 
(doi:10.5258/ecrystals/946)

More at:
http://ecrystals.chem.soton.ac.uk/946/

The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to the built-in table from CIF Core dictionary named
'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_values 3271 2015-04-21 07:52:19Z andrius 
;
_cod_original_sg_symbol_H-M      P2(1)/n
_cod_database_code               1519526
loop_
_symmetry_equiv_pos_as_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Br1 Br 0.21947(6) 0.835350(18) 0.47069(2) 0.02970(17) Uani 1 1 d . . .
C7 C -0.7476(7) 0.66330(16) 0.1443(2) 0.0235(7) Uani 1 1 d . . .
N1 N -0.6414(5) 0.59956(14) 0.16307(19) 0.0232(6) Uani 1 1 d . . .
N2 N -0.6308(5) 0.71334(13) 0.19675(19) 0.0219(6) Uani 1 1 d . . .
C4 C -0.0776(7) 0.66251(17) 0.3597(3) 0.0258(8) Uani 1 1 d . . .
C5 C -0.2549(6) 0.70988(18) 0.3188(2) 0.0231(7) Uani 1 1 d . . .
C3 C -0.0841(7) 0.58935(18) 0.3364(2) 0.0261(7) Uani 1 1 d . . .
C2 C -0.2631(6) 0.56116(19) 0.2718(2) 0.0250(7) Uani 1 1 d . . .
C9 C -0.6909(7) 0.79033(17) 0.1984(3) 0.0252(8) Uani 1 1 d . . .
C12 C -1.1342(8) 0.9129(2) 0.0424(3) 0.0326(8) Uani 1 1 d . . .
C1 C -0.4406(6) 0.60881(16) 0.2300(2) 0.0224(7) Uani 1 1 d . . .
C8 C -0.7145(8) 0.53227(19) 0.1151(3) 0.0304(8) Uani 1 1 d . . .
C6 C -0.4336(6) 0.68164(17) 0.2528(2) 0.0218(7) Uani 1 1 d . . .
C10 C -0.8793(7) 0.81132(19) 0.1180(3) 0.0263(8) Uani 1 1 d . . .
C11 C -0.9361(7) 0.89163(18) 0.1198(3) 0.0281(8) Uani 1 1 d . . .
O1W O 0.7165(6) 0.90407(15) 0.3459(2) 0.0400(7) Uani 1 1 d . . .
H9A H -0.751(6) 0.8025(18) 0.263(3) 0.022(8) Uiso 1 1 d . . .
H7 H -0.884(6) 0.6687(14) 0.098(2) 0.014(8) Uiso 1 1 d . . .
H12A H -1.067(6) 0.9020(17) -0.023(3) 0.022(9) Uiso 1 1 d . . .
H11B H -1.003(6) 0.8998(17) 0.181(3) 0.022(9) Uiso 1 1 d . . .
H3 H 0.045(7) 0.5599(18) 0.367(2) 0.028(9) Uiso 1 1 d . . .
H10A H -0.814(7) 0.7991(18) 0.051(3) 0.028(9) Uiso 1 1 d . . .
H12C H -1.299(7) 0.8873(17) 0.050(2) 0.019(8) Uiso 1 1 d . . .
H5 H -0.250(7) 0.758(2) 0.339(2) 0.030(9) Uiso 1 1 d . . .
H4 H 0.047(8) 0.6791(18) 0.401(3) 0.028(10) Uiso 1 1 d . . .
H10B H -1.044(7) 0.7848(18) 0.122(2) 0.025(9) Uiso 1 1 d . . .
H9B H -0.526(8) 0.817(2) 0.194(3) 0.041(11) Uiso 1 1 d . . .
H11A H -0.773(8) 0.916(2) 0.111(3) 0.040(10) Uiso 1 1 d . . .
H8A H -0.844(10) 0.541(2) 0.070(3) 0.060(13) Uiso 1 1 d . . .
H2 H -0.266(7) 0.5164(18) 0.253(2) 0.023(9) Uiso 1 1 d . . .
H8B H -0.770(7) 0.497(2) 0.163(3) 0.041(11) Uiso 1 1 d . . .
H12B H -1.169(7) 0.963(2) 0.045(3) 0.037(10) Uiso 1 1 d . . .
H8C H -0.574(9) 0.513(2) 0.085(3) 0.044(12) Uiso 1 1 d . . .
H1WA H 0.600(9) 0.889(2) 0.368(3) 0.038(14) Uiso 1 1 d . . .
H1WB H 0.846(10) 0.892(3) 0.382(4) 0.062(15) Uiso 1 1 d . . .
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
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
N2 C7 N1 110.4(3) . .
N2 C7 H7 128.1(17) . .
N1 C7 H7 121.4(17) . .
C7 N1 C1 108.3(3) . .
C7 N1 C8 125.4(3) . .
C1 N1 C8 126.1(3) . .
C7 N2 C6 108.6(3) . .
C7 N2 C9 127.5(3) . .
C6 N2 C9 123.9(3) . .
C5 C4 C3 121.2(3) . .
C5 C4 H4 119(2) . .
C3 C4 H4 119(2) . .
C4 C5 C6 116.4(3) . .
C4 C5 H5 119(2) . .
C6 C5 H5 125(2) . .
C2 C3 C4 122.4(3) . .
C2 C3 H3 121(2) . .
C4 C3 H3 117(2) . .
C3 C2 C1 116.5(3) . .
C3 C2 H2 124(2) . .
C1 C2 H2 119(2) . .
N2 C9 C10 112.0(3) . .
N2 C9 H9A 108(2) . .
C10 C9 H9A 113.8(19) . .
N2 C9 H9B 108(2) . .
C10 C9 H9B 111(2) . .
H9A C9 H9B 103(3) . .
C11 C12 H12A 110.4(19) . .
C11 C12 H12C 111.2(19) . .
H12A C12 H12C 108(3) . .
C11 C12 H12B 111(2) . .
H12A C12 H12B 108(3) . .
H12C C12 H12B 108(3) . .
N1 C1 C2 132.1(3) . .
N1 C1 C6 106.7(3) . .
C2 C1 C6 121.2(3) . .
N1 C8 H8A 110(3) . .
N1 C8 H8B 110(2) . .
H8A C8 H8B 111(4) . .
N1 C8 H8C 110(2) . .
H8A C8 H8C 109(4) . .
H8B C8 H8C 106(3) . .
C5 C6 N2 131.8(3) . .
C5 C6 C1 122.3(3) . .
N2 C6 C1 106.0(3) . .
C9 C10 C11 111.3(3) . .
C9 C10 H10A 113.4(19) . .
C11 C10 H10A 107(2) . .
C9 C10 H10B 111.6(19) . .
C11 C10 H10B 109.5(19) . .
H10A C10 H10B 103(3) . .
C12 C11 C10 111.9(3) . .
C12 C11 H11B 110(2) . .
C10 C11 H11B 104(2) . .
C12 C11 H11A 111(2) . .
C10 C11 H11A 108(2) . .
H11B C11 H11A 111(3) . .
H1WA O1W H1WB 106(5) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
C7 N2 1.320(4) .
C7 N1 1.334(4) .
C7 H7 0.94(3) .
N1 C1 1.380(4) .
N1 C8 1.467(4) .
N2 C6 1.392(4) .
N2 C9 1.473(4) .
C4 C5 1.381(5) .
C4 C3 1.406(5) .
C4 H4 0.90(4) .
C5 C6 1.383(5) .
C5 H5 0.94(4) .
C3 C2 1.372(5) .
C3 H3 0.95(4) .
C2 C1 1.390(5) .
C2 H2 0.87(3) .
C9 C10 1.507(5) .
C9 H9A 0.97(3) .
C9 H9B 0.97(4) .
C12 C11 1.511(5) .
C12 H12A 0.99(3) .
C12 H12C 0.98(3) .
C12 H12B 0.95(4) .
C1 C6 1.398(4) .
C8 H8A 0.92(5) .
C8 H8B 0.98(4) .
C8 H8C 0.91(4) .
C10 C11 1.530(5) .
C10 H10A 1.01(4) .
C10 H10B 0.98(3) .
C11 H11B 0.93(3) .
C11 H11A 0.96(4) .
O1W H1WA 0.73(4) .
O1W H1WB 0.85(5) .
