#------------------------------------------------------------------------------
#$Date: 2016-03-26 13:44:51 +0200 (Sat, 26 Mar 2016) $
#$Revision: 180234 $
#$URL: svn://www.crystallography.net/cod/cif/7/11/20/7112066.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_7112066
loop_
_publ_author_name
'Iain D. Roy'
'Alan R. Burns'
'Graham Pattison'
'Boris Michel'
'Alexandra J. Parker'
'Hon Wai Lam'
_publ_section_title
;
 A second-generation ligand for the enantioselective rhodium-catalyzed
 addition of arylboronic acids to alkenylazaarenes
;
_journal_name_full               Chem.Commun.
_journal_page_first              2865
_journal_paper_doi               10.1039/c4cc00340c
_journal_volume                  50
_journal_year                    2014
_chemical_formula_moiety         'C10 H10 N4'
_chemical_formula_sum            'C10 H10 N4'
_chemical_formula_weight         186.22
_chemical_name_systematic
;
 ?
;
_space_group_crystal_system      orthorhombic
_space_group_IT_number           61
_space_group_name_Hall           '-P 2ac 2ab'
_space_group_name_H-M_alt        'P b c a'
_symmetry_space_group_name_Hall  '-P 2ac 2ab'
_symmetry_space_group_name_H-M   'P b c a'
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2013
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   9.3737(2)
_cell_length_b                   8.5684(2)
_cell_length_c                   23.0087(6)
_cell_measurement_reflns_used    8026
_cell_measurement_temperature    120(2)
_cell_measurement_theta_max      30.7400
_cell_measurement_theta_min      3.6510
_cell_volume                     1848.00(8)
_computing_cell_refinement       'CrysAlisPro (Agilent Technologies, 2011)'
_computing_data_collection       'CrysAlisPro (Agilent Technologies, 2011)'
_computing_data_reduction        'CrysAlisPro (Agilent Technologies, 2011)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material
'SHELXTL (Sheldrick, 2008) and local programs'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_structure_solution    'SHELXTL (Sheldrick, 2008)'
_diffrn_ambient_temperature      120(2)
_diffrn_detector_area_resol_mean 10.3147
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.942
_diffrn_measurement_device_type  'Agilent Technologies SuperNova'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0319
_diffrn_reflns_av_unetI/netI     0.0214
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.942
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       33
_diffrn_reflns_limit_l_min       -32
_diffrn_reflns_number            19622
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.942
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         31.091
_diffrn_reflns_theta_min         2.803
_exptl_absorpt_coefficient_mu    0.086
_exptl_absorpt_correction_T_max  2.680
_exptl_absorpt_correction_T_min  1.468
_exptl_absorpt_correction_type   gaussian
_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)
Numerical absorption correction based on gaussian integration over
   a multifaceted crystal model
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.339
_exptl_crystal_description       block
_exptl_crystal_F_000             784
_exptl_crystal_size_max          0.584
_exptl_crystal_size_mid          0.532
_exptl_crystal_size_min          0.230
_refine_diff_density_max         0.344
_refine_diff_density_min         -0.211
_refine_diff_density_rms         0.046
_refine_ls_extinction_coef       0.0033(9)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.048
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     168
_refine_ls_number_reflns         2795
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.048
_refine_ls_R_factor_all          0.0513
_refine_ls_R_factor_gt           0.0431
_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)+(0.0533P)²+0.7566P]
 where P=(Fo²+2Fc²)/3
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1105
_refine_ls_wR_factor_ref         0.1172
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2373
_reflns_number_total             2795
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            c4cc00340c.txt
_cod_data_source_block           hl3010
_cod_database_code               7112066
#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   0.951
_shelx_estimated_absorpt_t_max   0.980
_shelxl_version_number           2013-2
#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, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'x, -y-1/2, z-1/2'
'-x-1/2, y-1/2, 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_site_symmetry_multiplicity
_atom_site_calc_flag
N1 N 0.58089(10) 0.16050(10) 0.45330(4) 0.0178(2) Uani 1 1 d
N2 N 0.63910(10) 0.09655(11) 0.50125(4) 0.0209(2) Uani 1 1 d
N3 N 0.72817(10) -0.00888(12) 0.48303(4) 0.0226(2) Uani 1 1 d
N4 N 0.72963(11) -0.01636(12) 0.42410(4) 0.0227(2) Uani 1 1 d
C1 C 0.63694(11) 0.09128(12) 0.40625(4) 0.0182(2) Uani 1 1 d
C2 C 0.60130(12) 0.12892(13) 0.34647(5) 0.0201(2) Uani 1 1 d
H2 H 0.5308(16) 0.2094(18) 0.3408(7) 0.030(4) Uiso 1 1 d
C3 C 0.66448(12) 0.05499(13) 0.30226(5) 0.0197(2) Uani 1 1 d
H3 H 0.7378(18) -0.0197(19) 0.3114(7) 0.032(4) Uiso 1 1 d
C4 C 0.64068(11) 0.07973(12) 0.24010(4) 0.0182(2) Uani 1 1 d
C5 C 0.73496(12) 0.00874(13) 0.20105(5) 0.0219(2) Uani 1 1 d
H5 H 0.8115(16) -0.0606(17) 0.2160(6) 0.029(4) Uiso 1 1 d
C7 C 0.72237(13) 0.03252(14) 0.14160(5) 0.0240(2) Uani 1 1 d
H7 H 0.7900(17) -0.0167(19) 0.1148(7) 0.035(4) Uiso 1 1 d
C8 C 0.61411(13) 0.12714(14) 0.12027(5) 0.0239(2) Uani 1 1 d
H8 H 0.6056(16) 0.1442(17) 0.0786(6) 0.028(4) Uiso 1 1 d
C9 C 0.51695(13) 0.19442(13) 0.15827(5) 0.0233(2) Uani 1 1 d
H9 H 0.4394(15) 0.2597(18) 0.1434(7) 0.028(4) Uiso 1 1 d
C10 C 0.52983(12) 0.17168(12) 0.21784(5) 0.0203(2) Uani 1 1 d
H10 H 0.4614(15) 0.2206(16) 0.2434(7) 0.028(4) Uiso 1 1 d
C11 C 0.47426(13) 0.28344(14) 0.45756(5) 0.0228(2) Uani 1 1 d
H11A H 0.511(2) 0.378(2) 0.4446(8) 0.056(5) Uiso 1 1 d
H11B H 0.389(2) 0.254(2) 0.4377(8) 0.052(5) Uiso 1 1 d
H11C H 0.4468(19) 0.298(2) 0.4973(9) 0.056(5) Uiso 1 1 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'
N N 0.0061 0.0033 '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
N2 N1 C1 108.80(9)
N2 N1 C11 121.15(9)
C1 N1 C11 130.04(9)
N1 N2 N3 106.19(9)
N2 N3 N4 111.19(9)
N3 N4 C1 105.59(9)
N1 C1 N4 108.23(9)
N1 C1 C2 125.18(10)
N4 C1 C2 126.58(10)
C1 C2 H2 116.4(9)
C1 C2 C3 120.92(10)
H2 C2 C3 122.7(9)
C2 C3 H3 117.7(9)
C2 C3 C4 127.42(10)
H3 C3 C4 114.8(9)
C3 C4 C5 117.93(10)
C3 C4 C10 123.51(10)
C5 C4 C10 118.56(10)
C4 C5 H5 119.6(8)
C4 C5 C7 121.01(11)
H5 C5 C7 119.4(8)
C5 C7 H7 120.1(9)
C5 C7 C8 119.74(11)
H7 C7 C8 120.2(9)
C7 C8 H8 119.7(9)
C7 C8 C9 119.96(10)
H8 C8 C9 120.3(9)
C8 C9 H9 120.3(9)
C8 C9 C10 120.41(11)
H9 C9 C10 119.3(9)
C4 C10 C9 120.26(10)
C4 C10 H10 120.9(9)
C9 C10 H10 118.8(9)
N1 C11 H11A 110.7(12)
N1 C11 H11B 110.6(11)
N1 C11 H11C 109.9(11)
H11A C11 H11B 112.9(17)
H11A C11 H11C 107.0(15)
H11B C11 H11C 105.4(15)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
N1 N2 1.3473(12)
N1 C1 1.3414(13)
N1 C11 1.4554(14)
N2 N3 1.2996(14)
N3 N4 1.3575(13)
N4 C1 1.3320(14)
C1 C2 1.4517(14)
C2 H2 0.964(15)
C2 C3 1.3367(15)
C3 H3 0.963(17)
C3 C4 1.4630(14)
C4 C5 1.3994(15)
C4 C10 1.4010(15)
C5 H5 0.993(15)
C5 C7 1.3882(15)
C7 H7 0.979(16)
C7 C8 1.3885(17)
C8 H8 0.973(15)
C8 C9 1.3879(17)
C9 H9 0.979(15)
C9 C10 1.3895(15)
C10 H10 0.966(15)
C11 H11A 0.93(2)
C11 H11B 0.953(19)
C11 H11C 0.96(2)
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
_geom_hbond_site_symmetry_A
C11 H11A N4 0.93(2) 2.63(2) 3.3525(16) 134.3(16) 8_765
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
C1 N1 N2 N3 -0.02(11)
C11 N1 N2 N3 179.51(9)
N1 N2 N3 N4 -0.24(12)
N2 N3 N4 C1 0.40(12)
N3 N4 C1 N1 -0.40(12)
N3 N4 C1 C2 179.59(10)
N2 N1 C1 N4 0.27(12)
N2 N1 C1 C2 -179.72(10)
C11 N1 C1 N4 -179.20(10)
C11 N1 C1 C2 0.80(18)
N1 C1 C2 C3 178.99(10)
N4 C1 C2 C3 -1.00(18)
C1 C2 C3 C4 -179.81(10)
C2 C3 C4 C5 169.43(11)
C2 C3 C4 C10 -9.87(18)
C3 C4 C5 C7 -177.26(10)
C10 C4 C5 C7 2.08(16)
C4 C5 C7 C8 -0.49(17)
C5 C7 C8 C9 -1.57(17)
C7 C8 C9 C10 2.00(17)
C8 C9 C10 C4 -0.38(17)
C3 C4 C10 C9 177.67(10)
C5 C4 C10 C9 -1.63(16)
