#------------------------------------------------------------------------------
#$Date: 2016-03-26 21:26:07 +0100 (Sat 26 de Mar de 2016) $
#$Revision: 180505 $
#$URL: svn://www.crystallography.net/cod/cif/7/21/74/7217457.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_7217457
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_formula_moiety         'C14 H10 Cl2 N2'
_chemical_formula_sum            'C14 H10 Cl2 N2'
_chemical_formula_weight         277.14
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_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-2013
_cell_angle_alpha                90.00
_cell_angle_beta                 94.316(1)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   5.7702(1)
_cell_length_b                   15.3388(2)
_cell_length_c                   13.9156(2)
_cell_measurement_reflns_used    8040
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      59.19
_cell_measurement_theta_min      2.65
_cell_volume                     1228.15(3)
_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      296(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.994
_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  0.0433
_diffrn_reflns_av_unetI/netI     0.0238
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            16883
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         67.827
_diffrn_reflns_theta_min         4.296
_exptl_absorpt_coefficient_mu    4.589
_exptl_absorpt_correction_T_max  0.753
_exptl_absorpt_correction_T_min  0.426
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Bruker, 2012)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.504
_exptl_crystal_description       'transparent rhomboid'
_exptl_crystal_F_000             568
_exptl_crystal_size_max          0.360
_exptl_crystal_size_mid          0.310
_exptl_crystal_size_min          0.250
_refine_diff_density_max         0.368
_refine_diff_density_min         -0.400
_refine_diff_density_rms         0.038
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.052
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     163
_refine_ls_number_reflns         2218
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.052
_refine_ls_R_factor_all          0.0518
_refine_ls_R_factor_gt           0.0382
_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)+(0.0433P)²+0.4521P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0958
_refine_ls_wR_factor_ref         0.1035
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1748
_reflns_number_total             2218
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            c4ce00323c2.cif
_cod_data_source_block           kaw78
_cod_database_code               7217457
#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   0.289
_shelx_estimated_absorpt_t_max   0.393
_shelxl_version_number           2013-4
#END Tags that were not found in dictionaries
loop_
_symmetry_equiv_pos_as_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
Cl1 Cl 0.61970(15) 0.38089(6) 1.00062(5) 0.0947(3) Uani 1 1 d . .
Cl2 Cl 0.05356(12) 0.31951(4) 0.17179(4) 0.0756(2) Uani 1 1 d . .
N1 N 0.9683(3) 0.43727(15) 0.61767(15) 0.0674(6) Uani 1 1 d . .
N2 N 0.6189(3) 0.38057(12) 0.54030(13) 0.0528(4) Uani 1 1 d . .
C1 C 0.8846(4) 0.41985(15) 0.70783(16) 0.0542(5) Uani 1 1 d . .
C2 C 1.0157(4) 0.44670(16) 0.79032(18) 0.0625(6) Uani 1 1 d . .
H2 H 1.1578 0.4740 0.7845 0.075 Uiso 1 1 calc R U
C3 C 0.9395(4) 0.43371(16) 0.87998(18) 0.0654(6) Uani 1 1 d . .
H3 H 1.0295 0.4513 0.9348 0.078 Uiso 1 1 calc R U
C4 C 0.7267(4) 0.39405(15) 0.88767(17) 0.0621(6) Uani 1 1 d . .
C5 C 0.5949(4) 0.36539(15) 0.80655(16) 0.0577(6) Uani 1 1 d . .
H5 H 0.4533 0.3378 0.8127 0.069 Uiso 1 1 calc R U
C6 C 0.6739(4) 0.37783(13) 0.71689(15) 0.0502(5) Uani 1 1 d . .
C7 C 0.5329(4) 0.34538(16) 0.62858(15) 0.0560(5) Uani 1 1 d . .
H7A H 0.5394 0.2822 0.6268 0.067 Uiso 1 1 calc R U
H7B H 0.3718 0.3623 0.6321 0.067 Uiso 1 1 calc R U
C8 C 0.8334(4) 0.41819(17) 0.54307(18) 0.0640(6) Uani 1 1 d . .
H8 H 0.8887 0.4316 0.4838 0.077 Uiso 1 1 calc R U
C9 C 0.4856(4) 0.36645(13) 0.45157(15) 0.0497(5) Uani 1 1 d . .
C10 C 0.5435(4) 0.40503(16) 0.36660(17) 0.0631(6) Uani 1 1 d . .
H10 H 0.6719 0.4417 0.3671 0.076 Uiso 1 1 calc R U
C11 C 0.4126(4) 0.38954(16) 0.28125(18) 0.0654(6) Uani 1 1 d . .
H11 H 0.4553 0.4148 0.2245 0.078 Uiso 1 1 calc R U
C12 C 0.2203(4) 0.33716(14) 0.27961(16) 0.0555(5) Uani 1 1 d . .
C13 C 0.1560(4) 0.29964(15) 0.36318(17) 0.0583(6) Uani 1 1 d . .
H13 H 0.0234 0.2651 0.3624 0.070 Uiso 1 1 calc R U
C14 C 0.2894(4) 0.31345(15) 0.44839(16) 0.0562(5) Uani 1 1 d . .
H14 H 0.2474 0.2869 0.5046 0.067 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'
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
C8 N1 C1 116.8(2)
C8 N2 C9 121.32(19)
C8 N2 C7 119.81(18)
C9 N2 C7 118.55(17)
C2 C1 C6 119.2(2)
C2 C1 N1 118.7(2)
C6 C1 N1 122.10(19)
C3 C2 C1 121.2(2)
C3 C2 H2 119.4
C1 C2 H2 119.4
C2 C3 C4 118.9(2)
C2 C3 H3 120.6
C4 C3 H3 120.6
C3 C4 C5 120.9(2)
C3 C4 Cl1 119.86(18)
C5 C4 Cl1 119.24(19)
C6 C5 C4 119.8(2)
C6 C5 H5 120.1
C4 C5 H5 120.1
C5 C6 C1 119.9(2)
C5 C6 C7 119.9(2)
C1 C6 C7 120.1(2)
N2 C7 C6 111.51(18)
N2 C7 H7A 109.3
C6 C7 H7A 109.3
N2 C7 H7B 109.3
C6 C7 H7B 109.3
H7A C7 H7B 108.0
N1 C8 N2 127.8(2)
N1 C8 H8 116.1
N2 C8 H8 116.1
C10 C9 C14 118.1(2)
C10 C9 N2 121.8(2)
C14 C9 N2 120.2(2)
C11 C10 C9 120.6(2)
C11 C10 H10 119.7
C9 C10 H10 119.7
C12 C11 C10 120.4(2)
C12 C11 H11 119.8
C10 C11 H11 119.8
C11 C12 C13 120.1(2)
C11 C12 Cl2 120.02(19)
C13 C12 Cl2 119.83(18)
C12 C13 C14 119.6(2)
C12 C13 H13 120.2
C14 C13 H13 120.2
C13 C14 C9 121.1(2)
C13 C14 H14 119.5
C9 C14 H14 119.5
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
Cl1 C4 1.743(3)
Cl2 C12 1.742(2)
N1 C8 1.283(3)
N1 C1 1.403(3)
N2 C8 1.364(3)
N2 C9 1.421(3)
N2 C7 1.462(3)
C1 C2 1.389(3)
C1 C6 1.390(3)
C2 C3 1.368(4)
C2 H2 0.9300
C3 C4 1.382(3)
C3 H3 0.9300
C4 C5 1.384(3)
C5 C6 1.373(3)
C5 H5 0.9300
C6 C7 1.507(3)
C7 H7A 0.9700
C7 H7B 0.9700
C8 H8 0.9300
C9 C10 1.385(3)
C9 C14 1.392(3)
C10 C11 1.379(3)
C10 H10 0.9300
C11 C12 1.369(3)
C11 H11 0.9300
C12 C13 1.373(3)
C13 C14 1.380(3)
C13 H13 0.9300
C14 H14 0.9300
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 C2 -174.2(2)
C8 N1 C1 C6 4.8(3)
C6 C1 C2 C3 -1.0(4)
N1 C1 C2 C3 178.1(2)
C1 C2 C3 C4 -0.8(4)
C2 C3 C4 C5 1.9(4)
C2 C3 C4 Cl1 -177.26(19)
C3 C4 C5 C6 -1.2(4)
Cl1 C4 C5 C6 177.97(17)
C4 C5 C6 C1 -0.6(3)
C4 C5 C6 C7 179.0(2)
C2 C1 C6 C5 1.7(3)
N1 C1 C6 C5 -177.4(2)
C2 C1 C6 C7 -177.9(2)
N1 C1 C6 C7 3.0(3)
C8 N2 C7 C6 15.3(3)
C9 N2 C7 C6 -171.17(18)
C5 C6 C7 N2 167.87(19)
C1 C6 C7 N2 -12.5(3)
C1 N1 C8 N2 -1.9(4)
C9 N2 C8 N1 177.5(2)
C7 N2 C8 N1 -9.1(4)
C8 N2 C9 C10 -13.1(3)
C7 N2 C9 C10 173.4(2)
C8 N2 C9 C14 167.6(2)
C7 N2 C9 C14 -5.8(3)
C14 C9 C10 C11 -1.4(3)
N2 C9 C10 C11 179.3(2)
C9 C10 C11 C12 1.4(4)
C10 C11 C12 C13 0.1(4)
C10 C11 C12 Cl2 178.93(19)
C11 C12 C13 C14 -1.5(3)
Cl2 C12 C13 C14 179.67(17)
C12 C13 C14 C9 1.4(3)
C10 C9 C14 C13 0.0(3)
N2 C9 C14 C13 179.3(2)
