#------------------------------------------------------------------------------
#$Date: 2016-03-21 04:38:07 +0200 (Mon, 21 Mar 2016) $
#$Revision: 178475 $
#$URL: svn://www.crystallography.net/cod/cif/4/02/96/4029658.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_4029658
loop_
_publ_author_name
'Bentley, Keith W.'
'Wolf, Christian'
_publ_contact_author             'Christian Wolf'
_publ_section_title
;
 Comprehensive Chirality Sensing: Development of Stereodynamic Probes with
 a Dual (Chir)optical Response.
;
_journal_issue                   14
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              6517
_journal_page_last               6531
_journal_paper_doi               10.1021/jo500959y
_journal_volume                  79
_journal_year                    2014
_chemical_formula_moiety         'C19 H12 Br N'
_chemical_formula_sum            'C19 H12 Br N'
_chemical_formula_weight         334.21
_chemical_name_common            '[isoquinyl-br]'
_chemical_name_systematic
;
 ?
;
_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
_cell_angle_beta                 105.512(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   7.9306(13)
_cell_length_b                   15.123(2)
_cell_length_c                   12.1926(19)
_cell_measurement_reflns_used    3466
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      28.3095
_cell_measurement_theta_min      2.195
_cell_volume                     1409.0(4)
_computing_cell_refinement       'Bruker APEXII'
_computing_data_collection       'Bruker APEXII'
_computing_data_reduction        'Bruker APEXII'
_computing_molecular_graphics
'ORTEP-3 for Windows; Ferrugia L J (1997), J. Appl. Cryst. 30, 565'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.970
_diffrn_measured_fraction_theta_max 0.903
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0161
_diffrn_reflns_av_unetI/netI     0.0219
_diffrn_reflns_Laue_measured_fraction_full 0.970
_diffrn_reflns_Laue_measured_fraction_max 0.903
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            6757
_diffrn_reflns_point_group_measured_fraction_full 0.970
_diffrn_reflns_point_group_measured_fraction_max 0.903
_diffrn_reflns_theta_full        25.000
_diffrn_reflns_theta_max         27.999
_diffrn_reflns_theta_min         2.195
_exptl_absorpt_coefficient_mu    2.908
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_correction_T_min  0.4999
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS based on Blessing's method; Blessing, Acta Cryst. (1995) A51 33-38'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.575
_exptl_crystal_description       plate
_exptl_crystal_F_000             672
_exptl_crystal_size_max          0.350
_exptl_crystal_size_mid          0.250
_exptl_crystal_size_min          0.160
_refine_diff_density_max         0.685
_refine_diff_density_min         -0.761
_refine_diff_density_rms         0.076
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.078
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     190
_refine_ls_number_reflns         3075
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.078
_refine_ls_R_factor_all          0.0386
_refine_ls_R_factor_gt           0.0319
_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)+(0.0503P)²+1.1758P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0904
_refine_ls_wR_factor_ref         0.0927
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2643
_reflns_number_total             3075
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            jo500959y_si_004.cif
_cod_data_source_block           isoquinyl-br
_cod_depositor_comments
'Adding full bibliography for 4029658--4029661.cif.'
_cod_original_cell_volume        1409.1(4)
_cod_database_code               4029658
#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   0.429
_shelx_estimated_absorpt_t_max   0.653
_shelxl_version_number           2013-4
#END Tags that were not found in dictionaries
loop_
_space_group_symop_operation_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
Br1 Br 0.59194(3) 0.24639(2) 0.49207(2) 0.02717(11) Uani 1 1 d . .
N1 N 0.9863(3) 0.37690(13) 0.38298(17) 0.0228(4) Uani 1 1 d . .
C19 C 0.9933(2) 0.20483(14) 0.47687(17) 0.0131(4) Uani 1 1 d . .
C17 C 1.0908(3) 0.35759(15) 0.48350(19) 0.0205(5) Uani 1 1 d . .
H17 H 1.1625 0.4036 0.5241 0.025 Uiso 1 1 calc R U
C9 C 0.6133(3) 0.11925(14) 0.31294(17) 0.0147(4) Uani 1 1 d . .
C1 C 0.7700(3) 0.15635(13) 0.29565(17) 0.0136(4) Uani 1 1 d . .
C2 C 0.8329(3) 0.12635(15) 0.20751(18) 0.0191(4) Uani 1 1 d . .
H2 H 0.9367 0.1518 0.1966 0.023 Uiso 1 1 calc R U
C16 C 0.8856(3) 0.30938(15) 0.32591(19) 0.0187(4) Uani 1 1 d . .
H16 H 0.8142 0.3213 0.2515 0.022 Uiso 1 1 calc R U
C13 C 1.1148(3) 0.10617(15) 0.63443(18) 0.0180(4) Uani 1 1 d . .
H13 H 1.1185 0.0497 0.6691 0.022 Uiso 1 1 calc R U
C18 C 1.1043(3) 0.27323(14) 0.53571(19) 0.0153(4) Uani 1 1 d . .
C4 C 0.6017(3) 0.02058(15) 0.14925(19) 0.0237(5) Uani 1 1 d . .
H4 H 0.5455 -0.0256 0.1001 0.028 Uiso 1 1 calc R U
C8 C 0.5262(3) 0.14573(15) 0.39684(19) 0.0196(4) Uani 1 1 d . .
C15 C 0.8801(3) 0.22582(14) 0.36816(18) 0.0136(4) Uani 1 1 d . .
C14 C 1.0010(3) 0.12101(14) 0.52971(18) 0.0145(4) Uani 1 1 d . .
H14 H 0.9267 0.0747 0.4923 0.017 Uiso 1 1 calc R U
C12 C 1.2267(3) 0.17411(15) 0.69125(18) 0.0196(5) Uani 1 1 d . .
H12 H 1.3059 0.1629 0.7634 0.023 Uiso 1 1 calc R U
C10 C 0.5318(3) 0.04874(15) 0.23912(19) 0.0199(5) Uani 1 1 d . .
C3 C 0.7480(3) 0.05879(15) 0.13254(19) 0.0234(5) Uani 1 1 d . .
H3 H 0.7927 0.0404 0.0713 0.028 Uiso 1 1 calc R U
C6 C 0.3075(3) 0.03227(19) 0.3375(3) 0.0373(7) Uani 1 1 d . .
H6 H 0.2075 0.0023 0.3477 0.045 Uiso 1 1 calc R U
C7 C 0.3799(3) 0.10247(19) 0.4094(2) 0.0302(6) Uani 1 1 d . .
H7 H 0.3276 0.1204 0.4674 0.036 Uiso 1 1 calc R U
C11 C 1.2216(3) 0.25572(14) 0.6431(2) 0.0183(5) Uani 1 1 d . .
H11 H 1.2974 0.3011 0.6819 0.022 Uiso 1 1 calc R U
C5 C 0.3793(3) 0.00676(18) 0.2534(2) 0.0309(6) Uani 1 1 d . .
H5 H 0.3268 -0.0397 0.2035 0.037 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 0.0033 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'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
C17 N1 C16 116.44(19)
C14 C19 C18 118.43(19)
C14 C19 C15 124.28(19)
C18 C19 C15 117.29(19)
N1 C17 C18 124.9(2)
C1 C9 C10 117.6(2)
C1 C9 C8 126.76(19)
C10 C9 C8 115.63(19)
C2 C1 C9 119.75(19)
C2 C1 C15 114.65(19)
C9 C1 C15 125.58(19)
C1 C2 C3 122.2(2)
N1 C16 C15 124.8(2)
C14 C13 C12 120.6(2)
C11 C18 C17 122.5(2)
C11 C18 C19 119.8(2)
C17 C18 C19 117.78(19)
C3 C4 C10 120.9(2)
C7 C8 C9 121.8(2)
C7 C8 Br1 114.48(19)
C9 C8 Br1 123.56(16)
C16 C15 C19 118.71(19)
C16 C15 C1 119.88(19)
C19 C15 C1 121.12(19)
C13 C14 C19 120.53(19)
C11 C12 C13 120.4(2)
C5 C10 C4 118.9(2)
C5 C10 C9 120.8(2)
C4 C10 C9 120.3(2)
C4 C3 C2 119.2(2)
C5 C6 C7 120.4(2)
C8 C7 C6 120.5(3)
C12 C11 C18 120.3(2)
C6 C5 C10 120.7(2)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
Br1 C8 1.901(2)
N1 C17 1.315(3)
N1 C16 1.367(3)
C19 C14 1.416(3)
C19 C18 1.422(3)
C19 C15 1.424(3)
C17 C18 1.417(3)
C9 C1 1.430(3)
C9 C10 1.433(3)
C9 C8 1.436(3)
C1 C2 1.377(3)
C1 C15 1.495(3)
C2 C3 1.416(3)
C16 C15 1.370(3)
C13 C14 1.371(3)
C13 C12 1.412(3)
C18 C11 1.414(3)
C4 C3 1.359(4)
C4 C10 1.419(4)
C8 C7 1.376(3)
C12 C11 1.363(3)
C10 C5 1.417(3)
C6 C5 1.355(4)
C6 C7 1.398(4)
