#------------------------------------------------------------------------------
#$Date: 2017-06-05 03:04:17 +0300 (Mon, 05 Jun 2017) $
#$Revision: 197384 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/54/62/1546239.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_1546239
loop_
_publ_author_name
'Zhu, Zhengbo'
'Seidel, Daniel'
_publ_section_title
;
 Acetic Acid Promoted Redox Annulations with Dual C-H Functionalization.
;
_journal_issue                   11
_journal_name_full               'Organic letters'
_journal_page_first              2841
_journal_page_last               2844
_journal_paper_doi               10.1021/acs.orglett.7b01047
_journal_volume                  19
_journal_year                    2017
_chemical_absolute_configuration unk
_chemical_formula_sum            'C21 H20 N2'
_chemical_formula_weight         300.39
_space_group_crystal_system      trigonal
_space_group_IT_number           159
_space_group_name_Hall           'P 3 -2c'
_space_group_name_H-M_alt        'P 3 1 c'
_symmetry_space_group_name_Hall  'P 3 -2c'
_symmetry_space_group_name_H-M   'P 3 1 c'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2014/7
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                120
_cell_formula_units_Z            6
_cell_length_a                   18.6655(11)
_cell_length_b                   18.6655(11)
_cell_length_c                   8.1126(5)
_cell_measurement_reflns_used    8205
_cell_measurement_temperature    195(2)
_cell_measurement_theta_max      30.46
_cell_measurement_theta_min      2.52
_cell_volume                     2447.8(3)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  SHELXL-2014/7
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXL-2014/7 (Sheldrick, 2014)'
_diffrn_ambient_temperature      195(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Bruker APEX'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0409
_diffrn_reflns_av_unetI/netI     0.0537
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       25
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            11857
_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         28.714
_diffrn_reflns_theta_min         2.182
_diffrn_source                   'sealed tube'
_exptl_absorpt_coefficient_mu    0.072
_exptl_absorpt_correction_T_max  .9999
_exptl_absorpt_correction_T_min  .8815
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Bruker SAINT (SADABS)'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.223
_exptl_crystal_description       rod
_exptl_crystal_F_000             960
_exptl_crystal_size_max          0.380
_exptl_crystal_size_mid          0.210
_exptl_crystal_size_min          0.140
_refine_diff_density_max         0.220
_refine_diff_density_min         -0.191
_refine_diff_density_rms         0.036
_refine_ls_abs_structure_details
; 
 Flack x determined using 1495 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259). 
;
_refine_ls_abs_structure_Flack   -2.9(10)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.043
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     210
_refine_ls_number_reflns         4088
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.043
_refine_ls_R_factor_all          0.0516
_refine_ls_R_factor_gt           0.0449
_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)+(0.0486P)²+0.1210P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0995
_refine_ls_wR_factor_ref         0.1035
_reflns_Friedel_coverage         0.991
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     1.000
_reflns_number_gt                3718
_reflns_number_total             4088
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            ol7b01047_si_004.cif
_cod_data_source_block           c21h20n2_P31c
_cod_database_code               1546239
_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   0.973
_shelx_estimated_absorpt_t_max   0.990
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-y, x-y, z'
'-x+y, -x, z'
'y, x, z+1/2'
'x-y, -y, z+1/2'
'-x, -x+y, 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
N1 N 0.69854(14) 0.12204(14) 0.3905(3) 0.0285(5) Uani 1 1 d . .
N2 N 0.48919(16) -0.10053(15) 0.4812(3) 0.0315(6) Uani 1 1 d . .
C1 C 0.70387(17) 0.07645(17) 0.5325(4) 0.0296(6) Uani 1 1 d . .
H1 H 0.6934 0.0996 0.6349 0.036 Uiso 1 1 calc R U
C2 C 0.63578(17) -0.01445(16) 0.5159(4) 0.0303(6) Uani 1 1 d . .
H2A H 0.6535 -0.0417 0.4338 0.036 Uiso 1 1 calc R U
H2B H 0.6293 -0.0425 0.6231 0.036 Uiso 1 1 calc R U
C3 C 0.55330(17) -0.02575(17) 0.4646(4) 0.0276(6) Uani 1 1 d . .
C4 C 0.41321(18) -0.11411(18) 0.4342(3) 0.0312(6) Uani 1 1 d . .
C5 C 0.3436(2) -0.19405(19) 0.4573(5) 0.0407(8) Uani 1 1 d . .
H5 H 0.3507 -0.2365 0.5051 0.049 Uiso 1 1 calc R U
C6 C 0.2665(2) -0.2106(2) 0.4118(5) 0.0462(8) Uani 1 1 d . .
H6 H 0.2203 -0.2642 0.4293 0.055 Uiso 1 1 calc R U
C7 C 0.2551(2) -0.1484(2) 0.3389(6) 0.0525(10) Uani 1 1 d . .
H7 H 0.2011 -0.1603 0.3080 0.063 Uiso 1 1 calc R U
C8 C 0.3210(2) -0.0713(2) 0.3125(6) 0.0491(9) Uani 1 1 d . .
H8 H 0.3129 -0.0303 0.2602 0.059 Uiso 1 1 calc R U
C9 C 0.40138(19) -0.05198(19) 0.3627(4) 0.0357(7) Uani 1 1 d . .
C10 C 0.47219(18) 0.02764(19) 0.3471(4) 0.0362(7) Uani 1 1 d . .
H10 H 0.4671 0.0714 0.2995 0.043 Uiso 1 1 calc R U
C11 C 0.54766(17) 0.04207(17) 0.3997(4) 0.0291(6) Uani 1 1 d . .
C12 C 0.62301(17) 0.12762(16) 0.3923(4) 0.0302(6) Uani 1 1 d . .
H12 H 0.6207 0.1522 0.2844 0.036 Uiso 1 1 calc R U
C13 C 0.77231(19) 0.20309(19) 0.3703(5) 0.0412(8) Uani 1 1 d . .
H13A H 0.7848 0.2346 0.4747 0.049 Uiso 1 1 calc R U
H13B H 0.7628 0.2347 0.2834 0.049 Uiso 1 1 calc R U
C14 C 0.8442(2) 0.1916(2) 0.3230(6) 0.0520(9) Uani 1 1 d . .
H14A H 0.8337 0.1645 0.2137 0.062 Uiso 1 1 calc R U
H14B H 0.8953 0.2461 0.3154 0.062 Uiso 1 1 calc R U
C15 C 0.8554(2) 0.1391(2) 0.4496(5) 0.0407(7) Uani 1 1 d . .
C16 C 0.9325(2) 0.1449(2) 0.4727(6) 0.0534(10) Uani 1 1 d . .
H16 H 0.9779 0.1819 0.4060 0.064 Uiso 1 1 calc R U
C17 C 0.9442(2) 0.0985(3) 0.5888(6) 0.0575(11) Uani 1 1 d . .
H17 H 0.9971 0.1037 0.6029 0.069 Uiso 1 1 calc R U
C18 C 0.8782(2) 0.0439(2) 0.6853(5) 0.0504(9) Uani 1 1 d . .
H18 H 0.8856 0.0116 0.7666 0.060 Uiso 1 1 calc R U
C19 C 0.8015(2) 0.03661(19) 0.6632(4) 0.0385(7) Uani 1 1 d . .
H19 H 0.7563 -0.0016 0.7289 0.046 Uiso 1 1 calc R U
C20 C 0.78900(19) 0.08400(18) 0.5467(4) 0.0336(6) Uani 1 1 d . .
C21 C 0.6186(2) 0.18295(19) 0.5278(5) 0.0394(7) Uani 1 1 d . .
H21A H 0.6223 0.1619 0.6362 0.059 Uiso 1 1 calc R U
H21B H 0.5660 0.1826 0.5191 0.059 Uiso 1 1 calc R U
H21C H 0.6646 0.2396 0.5144 0.059 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
C13 N1 C12 111.7(2)
C13 N1 C1 112.8(2)
C12 N1 C1 112.4(2)
C3 N2 C4 118.6(2)
N1 C1 C20 112.0(2)
N1 C1 C2 108.3(2)
C20 C1 C2 110.9(2)
N1 C1 H1 108.5
C20 C1 H1 108.5
C2 C1 H1 108.5
C3 C2 C1 113.8(2)
C3 C2 H2A 108.8
C1 C2 H2A 108.8
C3 C2 H2B 108.8
C1 C2 H2B 108.8
H2A C2 H2B 107.7
N2 C3 C11 123.4(3)
N2 C3 C2 116.4(3)
C11 C3 C2 120.2(2)
N2 C4 C9 122.6(3)
N2 C4 C5 118.6(3)
C9 C4 C5 118.8(3)
C6 C5 C4 120.7(3)
C6 C5 H5 119.6
C4 C5 H5 119.6
C5 C6 C7 120.3(3)
C5 C6 H6 119.9
C7 C6 H6 119.9
C8 C7 C6 120.4(3)
C8 C7 H7 119.8
C6 C7 H7 119.8
C7 C8 C9 120.4(3)
C7 C8 H8 119.8
C9 C8 H8 119.8
C4 C9 C10 116.9(3)
C4 C9 C8 119.4(3)
C10 C9 C8 123.7(3)
C11 C10 C9 120.6(3)
C11 C10 H10 119.7
C9 C10 H10 119.7
C10 C11 C3 118.0(3)
C10 C11 C12 121.3(3)
C3 C11 C12 120.7(2)
N1 C12 C11 110.2(2)
N1 C12 C21 115.6(3)
C11 C12 C21 110.3(3)
N1 C12 H12 106.8
C11 C12 H12 106.8
C21 C12 H12 106.8
N1 C13 C14 109.0(3)
N1 C13 H13A 109.9
C14 C13 H13A 109.9
N1 C13 H13B 109.9
C14 C13 H13B 109.9
H13A C13 H13B 108.3
C15 C14 C13 110.0(3)
C15 C14 H14A 109.7
C13 C14 H14A 109.7
C15 C14 H14B 109.7
C13 C14 H14B 109.7
H14A C14 H14B 108.2
C20 C15 C16 118.8(3)
C20 C15 C14 120.3(3)
C16 C15 C14 120.9(3)
C17 C16 C15 121.7(4)
C17 C16 H16 119.1
C15 C16 H16 119.1
C16 C17 C18 119.3(3)
C16 C17 H17 120.3
C18 C17 H17 120.3
C19 C18 C17 119.8(4)
C19 C18 H18 120.1
C17 C18 H18 120.1
C18 C19 C20 121.4(3)
C18 C19 H19 119.3
C20 C19 H19 119.3
C19 C20 C15 118.9(3)
C19 C20 C1 119.3(3)
C15 C20 C1 121.8(3)
C12 C21 H21A 109.5
C12 C21 H21B 109.5
H21A C21 H21B 109.5
C12 C21 H21C 109.5
H21A C21 H21C 109.5
H21B C21 H21C 109.5
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
N1 C13 1.459(4)
N1 C12 1.465(4)
N1 C1 1.465(4)
N2 C3 1.315(4)
N2 C4 1.364(4)
C1 C20 1.528(4)
C1 C2 1.535(4)
C1 H1 1.0000
C2 C3 1.504(4)
C2 H2A 0.9900
C2 H2B 0.9900
C3 C11 1.423(4)
C4 C9 1.409(4)
C4 C5 1.418(4)
C5 C6 1.362(5)
C5 H5 0.9500
C6 C7 1.412(6)
C6 H6 0.9500
C7 C8 1.363(5)
C7 H7 0.9500
C8 C9 1.417(5)
C8 H8 0.9500
C9 C10 1.417(4)
C10 C11 1.364(4)
C10 H10 0.9500
C11 C12 1.512(4)
C12 C21 1.539(4)
C12 H12 1.0000
C13 C14 1.510(5)
C13 H13A 0.9900
C13 H13B 0.9900
C14 C15 1.505(5)
C14 H14A 0.9900
C14 H14B 0.9900
C15 C20 1.393(5)
C15 C16 1.400(5)
C16 C17 1.369(6)
C16 H16 0.9500
C17 C18 1.383(6)
C17 H17 0.9500
C18 C19 1.380(4)
C18 H18 0.9500
C19 C20 1.392(5)
C19 H19 0.9500
C21 H21A 0.9800
C21 H21B 0.9800
C21 H21C 0.9800
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
C13 N1 C1 C20 -42.4(3)
C12 N1 C1 C20 -169.8(2)
C13 N1 C1 C2 -165.0(2)
C12 N1 C1 C2 67.6(3)
N1 C1 C2 C3 -44.0(3)
C20 C1 C2 C3 -167.3(3)
C4 N2 C3 C11 -0.1(4)
C4 N2 C3 C2 -179.2(3)
C1 C2 C3 N2 -166.3(3)
C1 C2 C3 C11 14.5(4)
C3 N2 C4 C9 2.5(4)
C3 N2 C4 C5 -177.9(3)
N2 C4 C5 C6 -179.8(3)
C9 C4 C5 C6 -0.2(5)
C4 C5 C6 C7 0.8(6)
C5 C6 C7 C8 0.3(6)
C6 C7 C8 C9 -2.0(7)
N2 C4 C9 C10 -2.5(4)
C5 C4 C9 C10 177.9(3)
N2 C4 C9 C8 178.1(3)
C5 C4 C9 C8 -1.4(5)
C7 C8 C9 C4 2.5(6)
C7 C8 C9 C10 -176.8(4)
C4 C9 C10 C11 0.0(5)
C8 C9 C10 C11 179.3(4)
C9 C10 C11 C3 2.3(5)
C9 C10 C11 C12 -176.7(3)
N2 C3 C11 C10 -2.4(5)
C2 C3 C11 C10 176.7(3)
N2 C3 C11 C12 176.6(3)
C2 C3 C11 C12 -4.3(4)
C13 N1 C12 C11 175.5(3)
C1 N1 C12 C11 -56.5(3)
C13 N1 C12 C21 -58.6(4)
C1 N1 C12 C21 69.3(3)
C10 C11 C12 N1 -157.2(3)
C3 C11 C12 N1 23.8(4)
C10 C11 C12 C21 74.0(4)
C3 C11 C12 C21 -105.0(3)
C12 N1 C13 C14 -164.7(3)
C1 N1 C13 C14 67.6(4)
N1 C13 C14 C15 -56.0(4)
C13 C14 C15 C20 24.7(5)
C13 C14 C15 C16 -155.0(3)
C20 C15 C16 C17 -0.7(6)
C14 C15 C16 C17 179.1(4)
C15 C16 C17 C18 0.5(6)
C16 C17 C18 C19 0.3(6)
C17 C18 C19 C20 -0.9(5)
C18 C19 C20 C15 0.7(5)
C18 C19 C20 C1 -177.2(3)
C16 C15 C20 C19 0.0(5)
C14 C15 C20 C19 -179.7(3)
C16 C15 C20 C1 177.9(3)
C14 C15 C20 C1 -1.8(5)
N1 C1 C20 C19 -172.5(3)
C2 C1 C20 C19 -51.4(4)
N1 C1 C20 C15 9.6(4)
C2 C1 C20 C15 130.7(3)
