#------------------------------------------------------------------------------
#$Date: 2016-03-26 22:26:07 +0200 (Sat, 26 Mar 2016) $
#$Revision: 180505 $
#$URL: svn://www.crystallography.net/cod/cif/7/21/74/7217456.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_7217456
loop_
_publ_author_name
'Cross, Jacob T.'
'Rossi, Nicholas A.'
'Serafin, Mateusz'
'Wheeler, Kraig A.'
_publ_section_title
;
 Tröger's base quasiracemates and crystal packing tendencies
;
_journal_issue                   31
_journal_name_full               CrystEngComm
_journal_page_first              7251
_journal_paper_doi               10.1039/C4CE00323C
_journal_volume                  16
_journal_year                    2014
_chemical_absolute_configuration rm
_chemical_formula_moiety         'C15 H13 Br2 N2, Cl, C H Cl3'
_chemical_formula_sum            'C16 H14 Br2 Cl4 N2'
_chemical_formula_weight         535.91
_chemical_name_systematic
;
 ?
;
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_atom_sites_solution_hydrogens   mixed
_audit_creation_method           SHELXL-2013
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   8.4113(1)
_cell_length_b                   9.0495(1)
_cell_length_c                   25.1456(3)
_cell_measurement_reflns_used    9912
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      71.588
_cell_measurement_theta_min      3.515
_cell_volume                     1914.03(4)
_computing_cell_refinement       APEX2
_computing_data_collection       APEX2
_computing_data_reduction
;
SAINT (Bruker, 2010) and XPREP (Bruker, 2010)
;
_computing_molecular_graphics    'XSEED (Barbour, 2001)'
_computing_publication_material  'XSEED (Barbour, 2001)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_structure_solution    'SHELXL-2013 (Sheldrick, 2013)'
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean 8.33
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Bruker APEXII CCD'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0334
_diffrn_reflns_av_unetI/netI     0.0232
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       30
_diffrn_reflns_limit_l_min       -30
_diffrn_reflns_number            16667
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         68.214
_diffrn_reflns_theta_min         3.515
_exptl_absorpt_coefficient_mu    10.523
_exptl_absorpt_correction_T_max  0.684
_exptl_absorpt_correction_T_min  0.201
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Bruker, 2012)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.860
_exptl_crystal_description       'transparent block'
_exptl_crystal_F_000             1048
_exptl_crystal_size_max          0.479
_exptl_crystal_size_mid          0.240
_exptl_crystal_size_min          0.120
_refine_diff_density_max         0.754
_refine_diff_density_min         -0.669
_refine_diff_density_rms         0.156
_refine_ls_abs_structure_details
;
 Flack x determined using 1443 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.451(7)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.222
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     220
_refine_ls_number_reflns         3475
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.222
_refine_ls_R_factor_all          0.0280
_refine_ls_R_factor_gt           0.0278
_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)+(0.0607P)²+1.9080P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0940
_refine_ls_wR_factor_ref         0.0940
_reflns_Friedel_coverage         0.715
_reflns_Friedel_fraction_full    0.991
_reflns_Friedel_fraction_max     0.988
_reflns_number_gt                3460
_reflns_number_total             3475
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            c4ce00323c2.cif
_cod_data_source_block           kaw46
_cod_database_code               7217456
#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   0.081
_shelx_estimated_absorpt_t_max   0.365
_shelxl_version_number           2014-1
#END Tags that were not found in dictionaries
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'x+1/2, -y+1/2, -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 -0.16858(7) -0.46740(6) -0.00461(2) 0.01498(17) Uani 1 1 d . .
Br2 Br 0.51209(6) 0.35335(6) 0.05423(2) 0.01471(17) Uani 1 1 d . .
Cl1 Cl 0.12472(17) -0.01219(15) 0.29478(5) 0.0158(3) Uani 1 1 d . .
Cl2 Cl 0.6865(2) 0.03523(18) 0.31377(6) 0.0289(4) Uani 1 1 d . .
Cl3 Cl 0.5250(2) 0.23773(16) 0.38387(6) 0.0233(3) Uani 1 1 d . .
Cl4 Cl 0.4743(3) 0.25794(19) 0.27059(7) 0.0362(5) Uani 1 1 d . .
N1 N -0.1878(6) 0.1000(5) 0.12553(17) 0.0096(9) Uani 1 1 d . .
N2 N 0.0191(6) 0.0111(5) 0.18306(18) 0.0120(9) Uani 1 1 d D .
H1 H 0.060(8) 0.015(8) 0.2134(15) 0.014 Uiso 1 1 d D U
C1 C -0.1770(6) -0.0348(6) 0.0958(2) 0.0115(10) Uani 1 1 d . .
C2 C -0.2554(6) -0.0419(6) 0.0468(2) 0.0120(11) Uani 1 1 d . .
H2 H -0.3127 0.0416 0.0343 0.014 Uiso 1 1 calc R U
C3 C -0.2507(6) -0.1687(7) 0.0165(2) 0.0137(11) Uani 1 1 d . .
H3 H -0.3019 -0.1729 -0.0172 0.016 Uiso 1 1 calc R U
C4 C -0.1688(7) -0.2904(6) 0.0364(2) 0.0135(10) Uani 1 1 d . .
C5 C -0.0900(7) -0.2869(6) 0.0843(2) 0.0117(11) Uani 1 1 d . .
H5 H -0.0356 -0.3720 0.0969 0.014 Uiso 1 1 calc R U
C6 C -0.0907(6) -0.1560(6) 0.1146(2) 0.0108(10) Uani 1 1 d . .
C7 C 0.0029(7) -0.1481(6) 0.1654(2) 0.0135(11) Uani 1 1 d . .
H7A H 0.1097 -0.1913 0.1598 0.016 Uiso 1 1 calc R U
H7B H -0.0516 -0.2060 0.1934 0.016 Uiso 1 1 calc R U
C8 C -0.1443(6) 0.0802(6) 0.1804(2) 0.0113(10) Uani 1 1 d . .
H8A H -0.2227 0.0154 0.1982 0.014 Uiso 1 1 calc R U
H8B H -0.1438 0.1768 0.1988 0.014 Uiso 1 1 calc R U
C9 C -0.0922(6) 0.2199(6) 0.1017(2) 0.0106(11) Uani 1 1 d . .
H9A H -0.1251 0.3159 0.1170 0.013 Uiso 1 1 calc R U
H9B H -0.1111 0.2233 0.0629 0.013 Uiso 1 1 calc R U
C10 C 0.0831(6) 0.1947(6) 0.1124(2) 0.0096(10) Uani 1 1 d . .
C11 C 0.1968(7) 0.2711(6) 0.0838(2) 0.0111(11) Uani 1 1 d . .
H11 H 0.1655 0.3402 0.0573 0.013 Uiso 1 1 calc R U
C12 C 0.3565(7) 0.2467(6) 0.0938(2) 0.0118(11) Uani 1 1 d . .
C13 C 0.4074(6) 0.1492(6) 0.1323(2) 0.0125(11) Uani 1 1 d . .
H13 H 0.5176 0.1348 0.1387 0.015 Uiso 1 1 calc R U
C14 C 0.2947(7) 0.0724(6) 0.1615(2) 0.0124(11) Uani 1 1 d . .
H14 H 0.3268 0.0048 0.1883 0.015 Uiso 1 1 calc R U
C15 C 0.1335(7) 0.0953(6) 0.1512(2) 0.0110(11) Uani 1 1 d . .
C16 C 0.5097(8) 0.1362(7) 0.3241(2) 0.0220(13) Uani 1 1 d . .
H16 H 0.4186 0.0656 0.3271 0.026 Uiso 1 1 calc R U
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.6763 1.2805 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.3639 0.7018 '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
C1 N1 C8 112.2(4)
C1 N1 C9 112.3(4)
C8 N1 C9 110.0(4)
C15 N2 C8 110.9(4)
C15 N2 C7 113.2(4)
C8 N2 C7 107.4(4)
C15 N2 H1 102(5)
C8 N2 H1 114(5)
C7 N2 H1 110(5)
C6 C1 C2 120.4(5)
C6 C1 N1 121.7(5)
C2 C1 N1 118.0(5)
C3 C2 C1 120.8(5)
C3 C2 H2 119.6
C1 C2 H2 119.6
C2 C3 C4 118.2(5)
C2 C3 H3 120.9
C4 C3 H3 120.9
C5 C4 C3 122.4(5)
C5 C4 Br1 119.5(4)
C3 C4 Br1 118.1(4)
C4 C5 C6 119.4(5)
C4 C5 H5 120.3
C6 C5 H5 120.3
C1 C6 C5 118.7(5)
C1 C6 C7 121.5(5)
C5 C6 C7 119.8(5)
C6 C7 N2 110.0(4)
C6 C7 H7A 109.7
N2 C7 H7A 109.7
C6 C7 H7B 109.7
N2 C7 H7B 109.7
H7A C7 H7B 108.2
N1 C8 N2 109.0(4)
N1 C8 H8A 109.9
N2 C8 H8A 109.9
N1 C8 H8B 109.9
N2 C8 H8B 109.9
H8A C8 H8B 108.3
N1 C9 C10 110.3(5)
N1 C9 H9A 109.6
C10 C9 H9A 109.6
N1 C9 H9B 109.6
C10 C9 H9B 109.6
H9A C9 H9B 108.1
C11 C10 C15 118.5(5)
C11 C10 C9 120.4(5)
C15 C10 C9 121.1(5)
C10 C11 C12 119.8(5)
C10 C11 H11 120.1
C12 C11 H11 120.1
C13 C12 C11 122.1(5)
C13 C12 Br2 118.5(4)
C11 C12 Br2 119.3(4)
C12 C13 C14 118.7(5)
C12 C13 H13 120.6
C14 C13 H13 120.6
C13 C14 C15 119.5(5)
C13 C14 H14 120.3
C15 C14 H14 120.3
C10 C15 C14 121.4(5)
C10 C15 N2 121.3(5)
C14 C15 N2 117.3(5)
Cl2 C16 Cl4 110.6(4)
Cl2 C16 Cl3 109.5(3)
Cl4 C16 Cl3 109.7(3)
Cl2 C16 H16 109.0
Cl4 C16 H16 109.0
Cl3 C16 H16 109.0
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
Br1 C4 1.905(5)
Br2 C12 1.906(5)
Cl2 C16 1.765(7)
Cl3 C16 1.766(6)
Cl4 C16 1.765(6)
N1 C1 1.433(7)
N1 C8 1.438(7)
N1 C9 1.477(7)
N2 C15 1.466(7)
N2 C8 1.512(7)
N2 C7 1.513(7)
N2 H1 0.84(3)
C1 C6 1.397(8)
C1 C2 1.398(8)
C2 C3 1.379(8)
C2 H2 0.9500
C3 C4 1.393(8)
C3 H3 0.9500
C4 C5 1.375(8)
C5 C6 1.408(8)
C5 H5 0.9500
C6 C7 1.503(7)
C7 H7A 0.9900
C7 H7B 0.9900
C8 H8A 0.9900
C8 H8B 0.9900
C9 C10 1.516(7)
C9 H9A 0.9900
C9 H9B 0.9900
C10 C11 1.382(8)
C10 C15 1.393(8)
C11 C12 1.385(8)
C11 H11 0.9500
C12 C13 1.377(8)
C13 C14 1.386(8)
C13 H13 0.9500
C14 C15 1.396(8)
C14 H14 0.9500
C16 H16 1.0000
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
N2 H1 Cl1 0.84(3) 2.13(3) 2.954(5) 167(7)
C16 H16 Cl1 1.00 2.70 3.582(6) 147.9
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
C8 N1 C1 C6 -17.4(7)
C9 N1 C1 C6 107.1(6)
C8 N1 C1 C2 162.8(5)
C9 N1 C1 C2 -72.7(6)
C6 C1 C2 C3 0.7(8)
N1 C1 C2 C3 -179.5(5)
C1 C2 C3 C4 1.5(8)
C2 C3 C4 C5 -1.7(8)
C2 C3 C4 Br1 177.9(4)
C3 C4 C5 C6 -0.2(8)
Br1 C4 C5 C6 -179.9(4)
C2 C1 C6 C5 -2.6(8)
N1 C1 C6 C5 177.6(5)
C2 C1 C6 C7 176.2(5)
N1 C1 C6 C7 -3.6(8)
C4 C5 C6 C1 2.4(8)
C4 C5 C6 C7 -176.4(5)
C1 C6 C7 N2 -13.3(7)
C5 C6 C7 N2 165.4(5)
C15 N2 C7 C6 -74.5(6)
C8 N2 C7 C6 48.2(5)
C1 N1 C8 N2 54.4(6)
C9 N1 C8 N2 -71.3(5)
C15 N2 C8 N1 52.4(5)
C7 N2 C8 N1 -71.7(5)
C1 N1 C9 C10 -74.7(6)
C8 N1 C9 C10 51.0(6)
N1 C9 C10 C11 164.5(5)
N1 C9 C10 C15 -16.0(7)
C15 C10 C11 C12 0.6(8)
C9 C10 C11 C12 -179.8(5)
C10 C11 C12 C13 -0.9(8)
C10 C11 C12 Br2 -179.8(4)
C11 C12 C13 C14 0.5(8)
Br2 C12 C13 C14 179.4(4)
C12 C13 C14 C15 0.2(8)
C11 C10 C15 C14 0.1(8)
C9 C10 C15 C14 -179.5(5)
C11 C10 C15 N2 179.8(5)
C9 C10 C15 N2 0.2(8)
C13 C14 C15 C10 -0.4(8)
C13 C14 C15 N2 179.8(5)
C8 N2 C15 C10 -17.8(7)
C7 N2 C15 C10 103.0(6)
C8 N2 C15 C14 162.0(5)
C7 N2 C15 C14 -77.3(6)
