#------------------------------------------------------------------------------
#$Date: 2015-06-04 22:30:53 +0200 (jue 04 de jun de 2015) $
#$Revision: 138011 $
#$URL: svn://www.crystallography.net/cod/cif/1/52/02/1520293.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_1520293
loop_
_publ_author_name
'Rumyantsev, Misha'
'Sitnikov, Nikolay S.'
'Somov, Nikolay V.'
_publ_section_title
;
 Hydrogen-bond-assisted organocatalytic acetalization of secondary
 alcohols: experimental and theoretical studies.
;
_journal_issue                   18
_journal_name_full               'The journal of physical chemistry. A'
_journal_page_first              4108
_journal_page_last               4117
_journal_paper_doi               10.1021/acs.jpca.5b02102
_journal_volume                  119
_journal_year                    2015
_chemical_absolute_configuration ad
_chemical_formula_sum            'C5 H5 Br2 N'
_chemical_formula_weight         238.90
_chemical_name_systematic
;
 ?
;
_space_group_IT_number           29
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2c -2ac'
_symmetry_space_group_name_H-M   'P c a 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_date             2013-09-10T12:48:51-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   14.2564(5)
_cell_length_b                   4.6063(2)
_cell_length_c                   10.7577(3)
_cell_measurement_reflns_used    4478
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      30.298
_cell_measurement_theta_min      3.761
_cell_volume                     706.45(4)
_computing_cell_refinement
;
        CrysAlisPro, Agilent Technologies,
        Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
        (compiled Feb  1 2013,16:14:44)
;
_computing_data_collection
;
        CrysAlisPro, Agilent Technologies,
        Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
        (compiled Feb  1 2013,16:14:44)
;
_computing_data_reduction
;
        CrysAlisPro, Agilent Technologies,
        Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
        (compiled Feb  1 2013,16:14:44)
;
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean 16.0302
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Xcalibur, Sapphire3, Gemini'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      -0.0007135
_diffrn_orient_matrix_UB_12      -0.150665
_diffrn_orient_matrix_UB_13      0.0135979
_diffrn_orient_matrix_UB_21      0.0484348
_diffrn_orient_matrix_UB_22      -0.00934
_diffrn_orient_matrix_UB_23      -0.0144767
_diffrn_orient_matrix_UB_31      0.0113096
_diffrn_orient_matrix_UB_32      0.0305053
_diffrn_orient_matrix_UB_33      0.0628767
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0387
_diffrn_reflns_av_unetI/netI     0.0241
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            10721
_diffrn_reflns_theta_full        28.26
_diffrn_reflns_theta_max         28.26
_diffrn_reflns_theta_min         3.43
_exptl_absorpt_coefficient_mu    11.37
_exptl_absorpt_correction_T_max  1
_exptl_absorpt_correction_T_min  0.217
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
        CrysAlisPro, Agilent Technologies,
        Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
        (compiled Feb  1 2013,16:14:44)
        Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_density_diffrn    2.246
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             448
_refine_diff_density_max         0.504
_refine_diff_density_min         -0.371
_refine_diff_density_rms         0.072
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.00(2)
_refine_ls_extinction_coef       0.0099(7)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.067
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     94
_refine_ls_number_reflns         1749
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.067
_refine_ls_R_factor_all          0.0308
_refine_ls_R_factor_gt           0.0256
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0297P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0548
_refine_ls_wR_factor_ref         0.0572
_reflns_number_gt                1598
_reflns_number_total             1749
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jp5b02102_si_002.cif
_cod_data_source_block           hydcla_br_090913
_cod_database_code               1520293
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, z+1/2'
'x+1/2, -y, z'
'-x+1/2, y, 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
C1 C 0.8063(3) -0.3110(10) 0.3719(5) 0.0483(11) Uani 1 1 d
C2 C 0.8032(3) -0.3973(8) 0.2489(5) 0.0433(9) Uani 1 1 d
C3 C 0.8674(3) -0.5954(8) 0.2097(3) 0.0353(8) Uani 1 1 d
C4 C 0.9325(3) -0.6275(9) 0.4073(4) 0.0429(9) Uani 1 1 d
C5 C 0.8707(3) -0.4272(11) 0.4524(4) 0.0512(10) Uani 1 1 d
N1 N 0.9301(2) -0.7080(6) 0.2875(3) 0.0357(7) Uani 1 1 d
Br1 Br 0.59861(3) 0.12559(8) 0.23531(3) 0.04411(12) Uani 1 1 d
Br2 Br 0.87324(3) -0.72426(10) 0.04355(5) 0.05049(13) Uani 1 1 d
H1 H 0.978(3) -0.831(6) 0.261(4) 0.028(9) Uiso 1 1 d
H2 H 0.760(3) -0.335(8) 0.190(4) 0.035(10) Uiso 1 1 d
H3 H 0.873(3) -0.379(10) 0.537(5) 0.056(13) Uiso 1 1 d
H4 H 0.761(4) -0.180(9) 0.390(5) 0.072(16) Uiso 1 1 d
H5 H 0.976(4) -0.713(9) 0.454(5) 0.066(15) Uiso 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 0.039(2) 0.049(2) 0.057(3) -0.006(2) 0.015(2) 0.0020(19)
C2 0.0304(17) 0.048(2) 0.052(2) 0.004(2) 0.002(2) 0.0009(15)
C3 0.0317(17) 0.0361(18) 0.038(2) -0.0001(15) -0.0013(14) -0.0092(13)
C4 0.041(2) 0.047(2) 0.041(2) -0.0002(18) -0.0057(18) -0.0028(18)
C5 0.053(2) 0.058(3) 0.043(2) -0.008(2) 0.004(2) -0.006(2)
N1 0.0315(16) 0.0370(15) 0.0388(17) 0.0006(13) -0.0011(14) -0.0016(14)
Br1 0.0445(2) 0.0437(2) 0.0441(2) -0.0014(2) 0.0028(2) -0.00659(16)
Br2 0.0488(2) 0.0627(3) 0.0400(2) -0.0054(2) -0.0039(2) -0.0013(2)
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 0 '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'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
C5 C1 C2 120.9(4)
C5 C1 H4 127(4)
C2 C1 H4 112(4)
C3 C2 C1 117.9(4)
C3 C2 H2 117(2)
C1 C2 H2 125(2)
N1 C3 C2 121.2(4)
N1 C3 Br2 116.4(3)
C2 C3 Br2 122.3(3)
N1 C4 C5 120.8(4)
N1 C4 H5 116(3)
C5 C4 H5 123(3)
C4 C5 C1 118.2(4)
C4 C5 H3 119(3)
C1 C5 H3 123(3)
C3 N1 C4 121.0(4)
C3 N1 H1 123(2)
C4 N1 H1 116(2)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C1 C5 1.371(7)
C1 C2 1.382(8)
C1 H4 0.91(5)
C2 C3 1.361(5)
C2 H2 0.93(4)
C3 N1 1.330(5)
C3 Br2 1.885(4)
C4 N1 1.341(5)
C4 C5 1.365(7)
C4 H5 0.89(5)
C5 H3 0.93(6)
N1 H1 0.93(4)
