#------------------------------------------------------------------------------
#$Date: 2016-02-13 14:50:18 +0200 (Sat, 13 Feb 2016) $
#$Revision: 176428 $
#$URL: svn://www.crystallography.net/cod/cif/1/51/95/1519580.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_1519580
loop_
_publ_author_name
'Butts, Craig'
'Coles, Simon J.'
'Hursthouse, Michael B.'
_publ_section_title
;
 C19H33BrN2O
;
_journal_name_full               'Crystal Structure Report Archive'
_journal_page_first              963
_journal_year                    2003
_chemical_formula_moiety         'C19 H31 N2, H2 O, Br'
_chemical_formula_sum            'C19 H33 Br N2 O'
_chemical_formula_weight         385.38
_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
_cell_angle_alpha                72.225(2)
_cell_angle_beta                 77.234(2)
_cell_angle_gamma                77.122(2)
_cell_formula_units_Z            2
_cell_length_a                   8.8931(3)
_cell_length_b                   9.0266(2)
_cell_length_c                   13.6881(6)
_cell_measurement_reflns_used    17263
_cell_measurement_temperature    120(2)
_cell_measurement_theta_max      27.48
_cell_measurement_theta_min      2.91
_cell_volume                     1006.10(6)
_computing_cell_refinement       'DENZO and COLLECT'
_computing_data_collection
;
'DENZO (Otwinowski and Minor, 1997) & COLLECT (Hooft, 1998) '
;
_computing_data_reduction        'DENZO and COLLECT'
_computing_publication_material  SHELXL-97
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      120(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Enraf Nonius KappaCCD area detector'
_diffrn_measurement_method       'ω and φ scans to fill Ewald sphere'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'Enraf Nonius FR591 rotating anode'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0727
_diffrn_reflns_av_sigmaI/netI    0.0500
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            20583
_diffrn_reflns_theta_full        27.50
_diffrn_reflns_theta_max         27.50
_diffrn_reflns_theta_min         2.96
_exptl_absorpt_coefficient_mu    2.050
_exptl_absorpt_correction_T_max  0.9898
_exptl_absorpt_correction_T_min  0.6390
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SORTAV (Blessing, 1997)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.272
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             408
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.01
_refine_diff_density_max         1.121
_refine_diff_density_min         -0.709
_refine_diff_density_rms         0.066
_refine_ls_extinction_coef       0.0062(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   1.020
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     217
_refine_ls_number_reflns         4615
_refine_ls_number_restraints     3
_refine_ls_restrained_S_all      1.022
_refine_ls_R_factor_all          0.0563
_refine_ls_R_factor_gt           0.0397
_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)+(0.0375P)²+0.6494P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0870
_refine_ls_wR_factor_ref         0.0935
_reflns_number_gt                3747
_reflns_number_total             4615
_reflns_threshold_expression     >2σ(I)
_cod_data_source_file            eCrystal-963.cif
_cod_data_source_block           s92
_cod_depositor_comments
;
Citation :
Butts, Craig and Coles, Simon J. and Hursthouse, Michael B. (2003) 
University of Southampton, Crystal Structure Report Archive. 
(doi:10.5258/ecrystals/963)

More at:
http://ecrystals.chem.soton.ac.uk/963/

The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic'
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      P-1
_cod_database_code               1519580
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
_atom_site_disorder_assembly
_atom_site_disorder_group
Br1 Br 0.16555(3) 0.12565(3) 0.57767(2) 0.03797(11) Uani 1 1 d . . .
N1 N 0.3896(2) 0.7603(2) 0.36325(15) 0.0238(4) Uani 1 1 d . . .
N2 N 0.2491(2) 0.5930(2) 0.35935(15) 0.0250(4) Uani 1 1 d . . .
C1 C 0.4172(4) 1.3564(4) -0.0978(2) 0.0534(8) Uani 1 1 d . . .
H1A H 0.4470 1.4420 -0.0802 0.080 Uiso 1 1 calc R . .
H1B H 0.3402 1.4006 -0.1449 0.080 Uiso 1 1 calc R . .
H1C H 0.5101 1.2984 -0.1320 0.080 Uiso 1 1 calc R . .
C2 C 0.3467(3) 1.2450(3) 0.0006(2) 0.0396(6) Uani 1 1 d . . .
H2A H 0.2517 1.3038 0.0339 0.047 Uiso 1 1 calc R . .
H2B H 0.3146 1.1603 -0.0180 0.047 Uiso 1 1 calc R . .
C3 C 0.4583(3) 1.1715(3) 0.0775(2) 0.0354(6) Uani 1 1 d . . .
H3A H 0.4938 1.2568 0.0933 0.042 Uiso 1 1 calc R . .
H3B H 0.5514 1.1098 0.0446 0.042 Uiso 1 1 calc R . .
C4 C 0.3901(3) 1.0645(3) 0.1785(2) 0.0331(5) Uani 1 1 d . . .
H4A H 0.3565 0.9776 0.1633 0.040 Uiso 1 1 calc R . .
H4B H 0.2963 1.1253 0.2114 0.040 Uiso 1 1 calc R . .
C5 C 0.5054(3) 0.9947(3) 0.2547(2) 0.0294(5) Uani 1 1 d . . .
H5A H 0.5911 0.9210 0.2258 0.035 Uiso 1 1 calc R . .
H5B H 0.5519 1.0810 0.2604 0.035 Uiso 1 1 calc R . .
C6 C 0.4354(3) 0.9076(3) 0.3624(2) 0.0293(5) Uani 1 1 d . . .
H6A H 0.5126 0.8829 0.4097 0.035 Uiso 1 1 calc R . .
H6B H 0.3423 0.9767 0.3889 0.035 Uiso 1 1 calc R . .
C7 C 0.2485(3) 0.7405(3) 0.35922(19) 0.0259(5) Uani 1 1 d . . .
H7 H 0.1588 0.8208 0.3566 0.031 Uiso 1 1 calc R . .
C8 C 0.4903(3) 0.6176(2) 0.36627(18) 0.0234(5) Uani 1 1 d . . .
C9 C 0.6486(3) 0.5730(3) 0.37308(19) 0.0271(5) Uani 1 1 d . . .
H9 H 0.7098 0.6455 0.3752 0.033 Uiso 1 1 calc R . .
C10 C 0.7113(3) 0.4184(3) 0.37657(19) 0.0291(5) Uani 1 1 d . . .
H10 H 0.8192 0.3831 0.3807 0.035 Uiso 1 1 calc R . .
C11 C 0.6206(3) 0.3108(3) 0.37419(19) 0.0297(5) Uani 1 1 d . . .
H11 H 0.6688 0.2048 0.3771 0.036 Uiso 1 1 calc R . .
C12 C 0.4642(3) 0.3548(3) 0.36775(19) 0.0277(5) Uani 1 1 d . . .
H12 H 0.4028 0.2822 0.3661 0.033 Uiso 1 1 calc R . .
C13 C 0.4009(3) 0.5109(3) 0.36377(17) 0.0235(5) Uani 1 1 d . . .
C14 C 0.1175(3) 0.5283(3) 0.3497(2) 0.0302(5) Uani 1 1 d . . .
H14A H 0.0183 0.5968 0.3685 0.036 Uiso 1 1 calc R . .
H14B H 0.1163 0.4221 0.3990 0.036 Uiso 1 1 calc R . .
C15 C 0.1281(3) 0.5165(3) 0.2402(2) 0.0315(5) Uani 1 1 d . . .
H15A H 0.0501 0.4531 0.2408 0.038 Uiso 1 1 calc R . .
H15B H 0.2330 0.4592 0.2188 0.038 Uiso 1 1 calc R . .
C16 C 0.1009(3) 0.6738(3) 0.1597(2) 0.0333(6) Uani 1 1 d . . .
H16A H 0.1771 0.7389 0.1597 0.040 Uiso 1 1 calc R . .
H16B H -0.0053 0.7302 0.1792 0.040 Uiso 1 1 calc R . .
C17 C 0.1172(3) 0.6559(3) 0.0510(2) 0.0360(6) Uani 1 1 d . . .
H17A H 0.2237 0.5994 0.0321 0.043 Uiso 1 1 calc R . .
H17B H 0.0418 0.5896 0.0518 0.043 Uiso 1 1 calc R . .
C18 C 0.0902(3) 0.8097(3) -0.0323(2) 0.0397(6) Uani 1 1 d . . .
H18A H -0.0175 0.8650 -0.0152 0.048 Uiso 1 1 calc R . .
H18B H 0.1635 0.8777 -0.0324 0.048 Uiso 1 1 calc R . .
C19 C 0.1123(4) 0.7872(4) -0.1396(2) 0.0559(8) Uani 1 1 d . . .
H19A H 0.2181 0.7308 -0.1566 0.084 Uiso 1 1 calc R . .
H19B H 0.0977 0.8904 -0.1905 0.084 Uiso 1 1 calc R . .
H19C H 0.0355 0.7257 -0.1414 0.084 Uiso 1 1 calc R . .
O1 O 1.0556(3) 0.1519(3) 0.3619(2) 0.0596(6) Uani 1 1 d D . .
H50 H 0.987(4) 0.085(4) 0.375(3) 0.089 Uiso 1 1 d D . .
H51 H 1.078(5) 0.143(5) 0.425(2) 0.089 Uiso 1 1 d 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'
Br Br -0.2901 2.4595 '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'
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
C7 N1 C8 108.21(18) . .
C7 N1 C6 126.63(18) . .
C8 N1 C6 125.15(18) . .
C7 N2 C13 107.86(18) . .
C7 N2 C14 126.92(19) . .
C13 N2 C14 125.11(18) . .
C2 C1 H1A 109.5 . .
C2 C1 H1B 109.5 . .
H1A C1 H1B 109.5 . .
C2 C1 H1C 109.5 . .
H1A C1 H1C 109.5 . .
H1B C1 H1C 109.5 . .
C3 C2 C1 112.8(2) . .
C3 C2 H2A 109.0 . .
C1 C2 H2A 109.0 . .
C3 C2 H2B 109.0 . .
C1 C2 H2B 109.0 . .
H2A C2 H2B 107.8 . .
C2 C3 C4 114.4(2) . .
C2 C3 H3A 108.7 . .
C4 C3 H3A 108.7 . .
C2 C3 H3B 108.7 . .
C4 C3 H3B 108.7 . .
H3A C3 H3B 107.6 . .
C3 C4 C5 112.8(2) . .
C3 C4 H4A 109.0 . .
C5 C4 H4A 109.0 . .
C3 C4 H4B 109.0 . .
C5 C4 H4B 109.0 . .
H4A C4 H4B 107.8 . .
C6 C5 C4 114.6(2) . .
C6 C5 H5A 108.6 . .
C4 C5 H5A 108.6 . .
C6 C5 H5B 108.6 . .
C4 C5 H5B 108.6 . .
H5A C5 H5B 107.6 . .
N1 C6 C5 112.03(19) . .
N1 C6 H6A 109.2 . .
C5 C6 H6A 109.2 . .
N1 C6 H6B 109.2 . .
C5 C6 H6B 109.2 . .
H6A C6 H6B 107.9 . .
N1 C7 N2 110.86(19) . .
N1 C7 H7 124.6 . .
N2 C7 H7 124.6 . .
C9 C8 C13 121.7(2) . .
C9 C8 N1 131.8(2) . .
C13 C8 N1 106.52(19) . .
C10 C9 C8 116.2(2) . .
C10 C9 H9 121.9 . .
C8 C9 H9 121.9 . .
C9 C10 C11 122.0(2) . .
C9 C10 H10 119.0 . .
C11 C10 H10 119.0 . .
C12 C11 C10 121.8(2) . .
C12 C11 H11 119.1 . .
C10 C11 H11 119.1 . .
C11 C12 C13 116.3(2) . .
C11 C12 H12 121.8 . .
C13 C12 H12 121.8 . .
C12 C13 C8 122.0(2) . .
C12 C13 N2 131.4(2) . .
C8 C13 N2 106.55(18) . .
N2 C14 C15 111.7(2) . .
N2 C14 H14A 109.3 . .
C15 C14 H14A 109.3 . .
N2 C14 H14B 109.3 . .
C15 C14 H14B 109.3 . .
H14A C14 H14B 107.9 . .
C14 C15 C16 114.6(2) . .
C14 C15 H15A 108.6 . .
C16 C15 H15A 108.6 . .
C14 C15 H15B 108.6 . .
C16 C15 H15B 108.6 . .
H15A C15 H15B 107.6 . .
C15 C16 C17 112.6(2) . .
C15 C16 H16A 109.1 . .
C17 C16 H16A 109.1 . .
C15 C16 H16B 109.1 . .
C17 C16 H16B 109.1 . .
H16A C16 H16B 107.8 . .
C18 C17 C16 114.7(2) . .
C18 C17 H17A 108.6 . .
C16 C17 H17A 108.6 . .
C18 C17 H17B 108.6 . .
C16 C17 H17B 108.6 . .
H17A C17 H17B 107.6 . .
C19 C18 C17 113.0(2) . .
C19 C18 H18A 109.0 . .
C17 C18 H18A 109.0 . .
C19 C18 H18B 109.0 . .
C17 C18 H18B 109.0 . .
H18A C18 H18B 107.8 . .
C18 C19 H19A 109.5 . .
C18 C19 H19B 109.5 . .
H19A C19 H19B 109.5 . .
C18 C19 H19C 109.5 . .
H19A C19 H19C 109.5 . .
H19B C19 H19C 109.5 . .
H50 O1 H51 104(3) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
N1 C7 1.321(3) .
N1 C8 1.390(3) .
N1 C6 1.471(3) .
N2 C7 1.329(3) .
N2 C13 1.392(3) .
N2 C14 1.466(3) .
C1 C2 1.516(4) .
C1 H1A 0.9800 .
C1 H1B 0.9800 .
C1 H1C 0.9800 .
C2 C3 1.508(4) .
C2 H2A 0.9900 .
C2 H2B 0.9900 .
C3 C4 1.512(4) .
C3 H3A 0.9900 .
C3 H3B 0.9900 .
C4 C5 1.522(3) .
C4 H4A 0.9900 .
C4 H4B 0.9900 .
C5 C6 1.512(3) .
C5 H5A 0.9900 .
C5 H5B 0.9900 .
C6 H6A 0.9900 .
C6 H6B 0.9900 .
C7 H7 0.9500 .
C8 C9 1.390(3) .
C8 C13 1.391(3) .
C9 C10 1.373(3) .
C9 H9 0.9500 .
C10 C11 1.405(3) .
C10 H10 0.9500 .
C11 C12 1.374(3) .
C11 H11 0.9500 .
C12 C13 1.385(3) .
C12 H12 0.9500 .
C14 C15 1.516(4) .
C14 H14A 0.9900 .
C14 H14B 0.9900 .
C15 C16 1.516(3) .
C15 H15A 0.9900 .
C15 H15B 0.9900 .
C16 C17 1.518(4) .
C16 H16A 0.9900 .
C16 H16B 0.9900 .
C17 C18 1.513(4) .
C17 H17A 0.9900 .
C17 H17B 0.9900 .
C18 C19 1.508(4) .
C18 H18A 0.9900 .
C18 H18B 0.9900 .
C19 H19A 0.9800 .
C19 H19B 0.9800 .
C19 H19C 0.9800 .
O1 H50 0.899(18) .
O1 H51 0.909(18) .
