#------------------------------------------------------------------------------
#$Date: 2019-11-24 04:54:56 +0200 (Sun, 24 Nov 2019) $
#$Revision: 236770 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/08/73/4087392.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_4087392
loop_
_publ_author_name
'Fontaine, Philip P.'
'Ueligger, Steve'
'Klosin, Jerzy'
'Hazari, Amaruka'
'Daller, Joe'
'Hou, Jianbo'
_publ_section_title
;
 Development of Improved Amidoquinoline Polyolefin Catalysts with
 Ultrahigh Molecular Weight Capacity
;
_journal_issue                   7
_journal_name_full               Organometallics
_journal_page_first              1354
_journal_paper_doi               10.1021/acs.organomet.5b00053
_journal_volume                  34
_journal_year                    2015
_chemical_formula_sum            'C19 H20 N2'
_chemical_formula_weight         276.37
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   mixed
_audit_creation_method           SHELXL-2014/7
_cell_angle_alpha                98.911(2)
_cell_angle_beta                 90.099(2)
_cell_angle_gamma                91.834(2)
_cell_formula_units_Z            2
_cell_length_a                   7.1032(2)
_cell_length_b                   8.6182(2)
_cell_length_c                   12.4141(4)
_cell_measurement_reflns_used    7847
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      29.85
_cell_measurement_theta_min      2.69
_cell_volume                     750.38(4)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0213
_diffrn_reflns_av_unetI/netI     0.0185
_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       -9
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            13826
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.497
_diffrn_reflns_theta_min         1.660
_exptl_absorpt_coefficient_mu    0.072
_exptl_absorpt_correction_T_max  0.991
_exptl_absorpt_correction_T_min  0.985
_exptl_absorpt_correction_type   multi-scan
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.223
_exptl_crystal_density_meas      0
_exptl_crystal_description       block
_exptl_crystal_F_000             296
_exptl_crystal_size_max          0.210
_exptl_crystal_size_mid          0.160
_exptl_crystal_size_min          0.130
_refine_diff_density_max         0.320
_refine_diff_density_min         -0.237
_refine_diff_density_rms         0.042
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.070
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     198
_refine_ls_number_reflns         3444
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.070
_refine_ls_R_factor_all          0.0544
_refine_ls_R_factor_gt           0.0431
_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)+(0.0596P)²+0.2301P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1154
_refine_ls_wR_factor_ref         0.1226
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2773
_reflns_number_total             3444
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            om5b00053_si_002.cif
_cod_data_source_block           7
_cod_database_code               4087392
_shelx_shelxl_version_number     2014/7
_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   0.985
_shelx_estimated_absorpt_t_max   0.991
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -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_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
N1 N 0.20757(15) 0.39354(13) 0.22157(9) 0.0223(2) Uani 1 1 d . .
H1 H 0.283(2) 0.475(2) 0.2446(14) 0.037(4) Uiso 1 1 d . .
N2 N 0.16169(14) 0.64042(12) 0.37870(8) 0.0193(2) Uani 1 1 d . .
C1 C 0.02715(17) 0.41753(14) 0.26290(10) 0.0193(3) Uani 1 1 d . .
C2 C -0.12936(17) 0.32516(14) 0.22678(10) 0.0216(3) Uani 1 1 d . .
H2 H -0.1176 0.2408 0.1683 0.026 Uiso 1 1 calc R U
C3 C -0.30667(17) 0.35421(15) 0.27545(10) 0.0232(3) Uani 1 1 d . .
H3 H -0.4128 0.2899 0.2484 0.028 Uiso 1 1 calc R U
C4 C -0.32909(17) 0.47323(15) 0.36102(10) 0.0225(3) Uani 1 1 d . .
H4 H -0.4491 0.4902 0.3936 0.027 Uiso 1 1 calc R U
C5 C -0.17132(17) 0.57071(14) 0.40039(10) 0.0194(3) Uani 1 1 d . .
C6 C 0.00587(17) 0.54606(14) 0.35006(9) 0.0184(3) Uani 1 1 d . .
C7 C -0.17875(18) 0.69561(14) 0.48879(10) 0.0217(3) Uani 1 1 d . .
H7 H -0.2928 0.7151 0.5277 0.026 Uiso 1 1 calc R U
C8 C -0.02159(18) 0.78808(14) 0.51804(10) 0.0219(3) Uani 1 1 d . .
H8 H -0.0258 0.8716 0.5776 0.026 Uiso 1 1 calc R U
C9 C 0.14757(17) 0.75902(14) 0.45938(10) 0.0203(3) Uani 1 1 d . .
C10 C 0.23288(16) 0.32390(15) 0.11024(10) 0.0208(3) Uani 1 1 d . .
C11 C 0.24998(16) 0.42165(14) 0.03013(10) 0.0215(3) Uani 1 1 d . .
C12 C 0.27100(17) 0.35277(15) -0.07779(10) 0.0229(3) Uani 1 1 d . .
H12 H 0.2826 0.4182 -0.1325 0.027 Uiso 1 1 calc R U
C13 C 0.27555(17) 0.19012(15) -0.10793(10) 0.0231(3) Uani 1 1 d . .
C14 C 0.26266(18) 0.09666(15) -0.02651(11) 0.0242(3) Uani 1 1 d . .
H14 H 0.2684 -0.0141 -0.0459 0.029 Uiso 1 1 calc R U
C15 C 0.24154(17) 0.16066(15) 0.08310(10) 0.0222(3) Uani 1 1 d . .
C17 C 0.24187(19) 0.59781(15) 0.06012(12) 0.0276(3) Uani 1 1 d . .
H17A H 0.2633 0.6470 -0.0051 0.041 Uiso 1 1 calc R U
H17B H 0.3393 0.6354 0.1148 0.041 Uiso 1 1 calc R U
H17C H 0.1177 0.6254 0.0901 0.041 Uiso 1 1 calc R U
C18 C 0.2279(2) 0.05430(16) 0.16881(11) 0.0287(3) Uani 1 1 d . .
H18A H 0.0959 0.0226 0.1777 0.043 Uiso 1 1 calc R U
H18B H 0.2775 0.1105 0.2382 0.043 Uiso 1 1 calc R U
H18C H 0.3016 -0.0393 0.1461 0.043 Uiso 1 1 calc R U
C19 C 0.2941(2) 0.12045(17) -0.22661(11) 0.0312(3) Uani 1 1 d . .
H19A H 0.3064 0.0065 -0.2330 0.047 Uiso 1 1 calc R U
H19B H 0.4060 0.1666 -0.2570 0.047 Uiso 1 1 calc R U
H19C H 0.1819 0.1430 -0.2668 0.047 Uiso 1 1 calc R U
C16 C 0.31964(19) 0.86321(15) 0.48734(11) 0.0258(3) Uani 1 1 d . .
H16A H 0.4202 0.8301 0.4357 0.039 Uiso 1 1 calc R U
H16B H 0.3617 0.8552 0.5615 0.039 Uiso 1 1 calc R U
H16C H 0.2895 0.9723 0.4831 0.039 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'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
C1 N1 C10 120.13(10)
C1 N1 H1 110.8(11)
C10 N1 H1 115.2(11)
C9 N2 C6 118.40(11)
C2 C1 N1 124.36(11)
C2 C1 C6 118.71(11)
N1 C1 C6 116.92(10)
C1 C2 C3 120.90(11)
C1 C2 H2 119.6
C3 C2 H2 119.6
C4 C3 C2 121.38(11)
C4 C3 H3 119.3
C2 C3 H3 119.3
C3 C4 C5 119.32(11)
C3 C4 H4 120.3
C5 C4 H4 120.3
C6 C5 C7 116.30(11)
C6 C5 C4 119.86(11)
C7 C5 C4 123.84(11)
N2 C6 C5 123.45(11)
N2 C6 C1 116.80(11)
C5 C6 C1 119.75(11)
C8 C7 C5 119.85(11)
C8 C7 H7 120.1
C5 C7 H7 120.1
C7 C8 C9 119.80(11)
C7 C8 H8 120.1
C9 C8 H8 120.1
N2 C9 C8 122.09(11)
N2 C9 C16 117.28(11)
C8 C9 C16 120.62(11)
C15 C10 C11 121.05(11)
C15 C10 N1 119.87(12)
C11 C10 N1 119.08(11)
C12 C11 C10 118.60(11)
C12 C11 C17 120.62(12)
C10 C11 C17 120.76(12)
C11 C12 C13 121.77(12)
C11 C12 H12 119.1
C13 C12 H12 119.1
C14 C13 C12 118.28(12)
C14 C13 C19 121.86(12)
C12 C13 C19 119.87(12)
C13 C14 C15 121.96(12)
C13 C14 H14 119.0
C15 C14 H14 119.0
C14 C15 C10 118.31(12)
C14 C15 C18 120.08(11)
C10 C15 C18 121.61(11)
C11 C17 H17A 109.5
C11 C17 H17B 109.5
H17A C17 H17B 109.5
C11 C17 H17C 109.5
H17A C17 H17C 109.5
H17B C17 H17C 109.5
C15 C18 H18A 109.5
C15 C18 H18B 109.5
H18A C18 H18B 109.5
C15 C18 H18C 109.5
H18A C18 H18C 109.5
H18B C18 H18C 109.5
C13 C19 H19A 109.5
C13 C19 H19B 109.5
H19A C19 H19B 109.5
C13 C19 H19C 109.5
H19A C19 H19C 109.5
H19B C19 H19C 109.5
C9 C16 H16A 109.5
C9 C16 H16B 109.5
H16A C16 H16B 109.5
C9 C16 H16C 109.5
H16A C16 H16C 109.5
H16B C16 H16C 109.5
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
N1 C1 1.3909(16)
N1 C10 1.4331(16)
N1 H1 0.877(18)
N2 C9 1.3220(15)
N2 C6 1.3653(15)
C1 C2 1.3791(17)
C1 C6 1.4355(16)
C2 C3 1.4107(18)
C2 H2 0.9500
C3 C4 1.3709(18)
C3 H3 0.9500
C4 C5 1.4182(17)
C4 H4 0.9500
C5 C6 1.4136(17)
C5 C7 1.4155(17)
C7 C8 1.3657(18)
C7 H7 0.9500
C8 C9 1.4151(17)
C8 H8 0.9500
C9 C16 1.5007(17)
C10 C15 1.3983(17)
C10 C11 1.4025(18)
C11 C12 1.3891(18)
C11 C17 1.5091(17)
C12 C13 1.3951(18)
C12 H12 0.9500
C13 C14 1.3880(18)
C13 C19 1.5100(17)
C14 C15 1.3971(17)
C14 H14 0.9500
C15 C18 1.5095(18)
C17 H17A 0.9800
C17 H17B 0.9800
C17 H17C 0.9800
C18 H18A 0.9800
C18 H18B 0.9800
C18 H18C 0.9800
C19 H19A 0.9800
C19 H19B 0.9800
C19 H19C 0.9800
C16 H16A 0.9800
C16 H16B 0.9800
C16 H16C 0.9800
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
N1 H1 N2 0.877(18) 2.214(17) 2.6831(14) 113.2(14)
N1 H1 N2 0.877(18) 2.214(17) 2.6831(14) 113.2(14)
N1 H1 N2 0.877(18) 2.214(17) 2.6831(14) 113.2(14)
N1 H1 N2 0.877(18) 2.214(17) 2.6831(14) 113.2(14)
N1 H1 N2 0.877(18) 2.214(17) 2.6831(14) 113.2(14)
N1 H1 N2 0.877(18) 2.214(17) 2.6831(14) 113.2(14)
N1 H1 N2 0.877(18) 2.214(17) 2.6831(14) 113.2(14)
N1 H1 N2 0.877(18) 2.214(17) 2.6831(14) 113.2(14)
N1 H1 N2 0.877(18) 2.214(17) 2.6831(14) 113.2(14)
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
C10 N1 C1 C2 29.67(18)
C10 N1 C1 C6 -151.36(11)
N1 C1 C2 C3 177.90(11)
C6 C1 C2 C3 -1.06(18)
C1 C2 C3 C4 -0.97(19)
C2 C3 C4 C5 0.96(18)
C3 C4 C5 C6 1.08(18)
C3 C4 C5 C7 -179.36(11)
C9 N2 C6 C5 1.60(17)
C9 N2 C6 C1 -179.36(10)
C7 C5 C6 N2 -3.67(17)
C4 C5 C6 N2 175.91(11)
C7 C5 C6 C1 177.32(10)
C4 C5 C6 C1 -3.09(17)
C2 C1 C6 N2 -176.01(10)
N1 C1 C6 N2 4.96(16)
C2 C1 C6 C5 3.06(17)
N1 C1 C6 C5 -175.97(10)
C6 C5 C7 C8 2.56(17)
C4 C5 C7 C8 -177.01(11)
C5 C7 C8 C9 0.36(18)
C6 N2 C9 C8 1.63(17)
C6 N2 C9 C16 -178.53(10)
C7 C8 C9 N2 -2.62(19)
C7 C8 C9 C16 177.54(11)
C1 N1 C10 C15 -89.71(15)
C1 N1 C10 C11 90.75(14)
C15 C10 C11 C12 1.63(17)
N1 C10 C11 C12 -178.84(11)
C15 C10 C11 C17 -179.57(11)
N1 C10 C11 C17 -0.04(17)
C10 C11 C12 C13 -0.04(18)
C17 C11 C12 C13 -178.84(11)
C11 C12 C13 C14 -1.43(19)
C11 C12 C13 C19 178.57(12)
C12 C13 C14 C15 1.36(19)
C19 C13 C14 C15 -178.63(12)
C13 C14 C15 C10 0.16(19)
C13 C14 C15 C18 179.94(12)
C11 C10 C15 C14 -1.69(18)
N1 C10 C15 C14 178.78(11)
C11 C10 C15 C18 178.53(11)
N1 C10 C15 C18 -0.99(18)
