#------------------------------------------------------------------------------
#$Date: 2016-02-18 17:37:37 +0200 (Thu, 18 Feb 2016) $
#$Revision: 176729 $
#$URL: svn://www.crystallography.net/cod/cif/1/51/83/1518304.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_1518304
loop_
_publ_author_name
'Fan, Yan-Sen'
'Jiang, Yi-Jun'
'An, Dong'
'Sha, Di'
'Antilla, Jon C.'
'Zhang, Suoqin'
_publ_section_title
;
 H8-BINOL Chiral Imidodiphosphoric Acids Catalyzed Enantioselective
 Synthesis of Dihydroindolo-/-pyrrolo[1,2-a]quinoxalines.
;
_journal_issue                   23
_journal_name_full               'Organic letters'
_journal_page_first              6112
_journal_paper_doi               10.1021/ol502965p
_journal_volume                  16
_journal_year                    2014
_chemical_absolute_configuration ad
_chemical_formula_sum            'C26 H21 Cl N2 O2'
_chemical_formula_weight         428.90
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           4
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 108.4300(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   13.8842(6)
_cell_length_b                   5.6862(2)
_cell_length_c                   14.2638(6)
_cell_measurement_temperature    296(2)
_cell_volume                     1068.35(7)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0249
_diffrn_reflns_av_sigmaI/netI    0.0483
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            9052
_diffrn_reflns_theta_full        28.34
_diffrn_reflns_theta_max         28.34
_diffrn_reflns_theta_min         1.50
_exptl_absorpt_coefficient_mu    0.205
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.333
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             448
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.134
_refine_diff_density_min         -0.226
_refine_diff_density_rms         0.033
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.01(9)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.017
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     364
_refine_ls_number_reflns         5173
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.017
_refine_ls_R_factor_all          0.0832
_refine_ls_R_factor_gt           0.0475
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0476P)²+0.0201P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0963
_refine_ls_wR_factor_ref         0.1138
_reflns_number_gt                3367
_reflns_number_total             5173
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol502965p_si_003.cif
_cod_data_source_block           1
_cod_depositor_comments
'Adding full bibliography for 1518303--1518304.cif.'
_cod_original_sg_symbol_H-M      P2(1)
_cod_database_code               1518304
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, 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_symmetry_multiplicity
_atom_site_calc_flag
C1 C 0.79490(17) 0.7277(4) -0.07739(16) 0.0420(5) Uani 1 1 d
C2 C 0.7688(2) 0.7084(5) -0.17997(18) 0.0532(6) Uani 1 1 d
C3 C 0.8021(2) 0.8725(6) -0.2331(2) 0.0596(7) Uani 1 1 d
C4 C 0.8602(2) 1.0600(5) -0.1866(2) 0.0614(7) Uani 1 1 d
C5 C 0.8867(2) 1.0825(5) -0.0849(2) 0.0533(6) Uani 1 1 d
C6 C 0.85506(16) 0.9157(4) -0.03054(15) 0.0413(5) Uani 1 1 d
C7 C 0.96048(17) 1.0483(4) 0.13809(19) 0.0482(6) Uani 1 1 d
C8 C 0.96422(19) 0.9911(5) 0.23103(19) 0.0509(6) Uani 1 1 d
C9 C 0.88768(16) 0.8232(4) 0.22710(15) 0.0435(5) Uani 1 1 d
C10 C 0.75065(16) 0.6269(4) 0.07209(15) 0.0376(5) Uani 1 1 d
C11 C 0.83865(15) 0.7809(4) 0.12785(15) 0.0382(5) Uani 1 1 d
C12 C 0.65305(16) 0.7753(4) 0.05099(15) 0.0392(5) Uani 1 1 d
C13 C 0.86610(18) 0.7156(4) 0.31271(15) 0.0472(6) Uani 1 1 d
C14 C 0.9206(2) 0.5236(5) 0.3615(2) 0.0650(8) Uani 1 1 d
C15 C 0.8972(3) 0.4169(7) 0.4383(2) 0.0791(9) Uani 1 1 d
C16 C 0.8202(2) 0.5025(6) 0.46813(18) 0.0703(9) Uani 1 1 d
C17 C 0.7664(3) 0.6955(8) 0.4233(2) 0.0884(11) Uani 1 1 d
C18 C 0.7907(2) 0.8033(7) 0.3470(2) 0.0715(9) Uani 1 1 d
C19 C 0.5250(2) 0.9115(7) 0.11389(19) 0.0583(7) Uani 1 1 d
C20 C 0.50636(17) 0.9249(5) 0.21112(16) 0.0471(6) Uani 1 1 d
C21 C 0.5421(2) 1.1167(6) 0.2709(2) 0.0645(7) Uani 1 1 d
C22 C 0.5269(3) 1.1303(8) 0.3620(3) 0.0844(10) Uani 1 1 d
C23 C 0.4746(3) 0.9605(8) 0.3912(2) 0.0833(11) Uani 1 1 d
C24 C 0.4376(3) 0.7710(8) 0.3327(3) 0.0797(10) Uani 1 1 d
C25 C 0.4542(2) 0.7511(6) 0.2412(2) 0.0626(7) Uani 1 1 d
C26 C 0.7421(2) 0.4019(4) 0.12730(19) 0.0465(6) Uani 1 1 d
Cl1 Cl 0.78784(8) 0.3626(2) 0.56243(6) 0.1161(4) Uani 1 1 d
H1 H 0.7310(18) 0.573(5) -0.2074(17) 0.058(8) Uiso 1 1 d
H2 H 0.7872(18) 0.860(6) -0.3010(18) 0.067(8) Uiso 1 1 d
H3 H 0.884(2) 1.163(6) -0.2238(19) 0.075(9) Uiso 1 1 d
H4 H 0.9261(18) 1.205(5) -0.0534(16) 0.049(7) Uiso 1 1 d
H5 H 1.0067(19) 1.147(5) 0.1106(16) 0.062(8) Uiso 1 1 d
H6 H 1.007(2) 1.048(5) 0.289(2) 0.072(9) Uiso 1 1 d
H7 H 0.7249(18) 0.456(5) -0.0554(16) 0.056(8) Uiso 1 1 d
H8 H 0.6892(18) 0.308(5) 0.0858(16) 0.048(7) Uiso 1 1 d
H9 H 0.808(2) 0.316(6) 0.1439(18) 0.078(9) Uiso 1 1 d
H10 H 0.7217(17) 0.433(5) 0.1872(17) 0.052(7) Uiso 1 1 d
H11 H 0.470(2) 0.835(6) 0.064(2) 0.076(9) Uiso 1 1 d
H12 H 0.532(2) 1.070(6) 0.089(2) 0.085(10) Uiso 1 1 d
H13 H 0.578(3) 1.241(8) 0.246(2) 0.119(14) Uiso 1 1 d
H14 H 0.430(2) 0.625(6) 0.202(2) 0.076(9) Uiso 1 1 d
H15 H 0.412(2) 0.660(7) 0.357(2) 0.082(11) Uiso 1 1 d
H16 H 0.762(2) 0.934(7) 0.320(2) 0.089(11) Uiso 1 1 d
H17 H 0.717(2) 0.759(7) 0.452(2) 0.107(12) Uiso 1 1 d
H18 H 0.932(3) 0.264(8) 0.464(2) 0.113(12) Uiso 1 1 d
H19 H 0.552(3) 1.282(9) 0.399(3) 0.144(16) Uiso 1 1 d
H20 H 0.462(2) 0.988(7) 0.453(2) 0.102(12) Uiso 1 1 d
H21 H 0.971(2) 0.469(6) 0.334(2) 0.090(11) Uiso 1 1 d
N1 N 0.76667(15) 0.5589(3) -0.02041(14) 0.0452(5) Uani 1 1 d
N2 N 0.88352(12) 0.9211(3) 0.07396(12) 0.0401(4) Uani 1 1 d
O1 O 0.61224(12) 0.8755(3) -0.02513(11) 0.0566(5) Uani 1 1 d
O2 O 0.61847(12) 0.7797(3) 0.12749(11) 0.0551(5) Uani 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'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 '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
C6 C1 N1 119.1(2)
C6 C1 C2 118.8(2)
N1 C1 C2 122.0(2)
C3 C2 C1 120.3(3)
C2 C3 C4 120.7(3)
C3 C4 C5 119.8(3)
C6 C5 C4 119.9(3)
C5 C6 C1 120.5(2)
C5 C6 N2 122.9(2)
C1 C6 N2 116.6(2)
C8 C7 N2 107.9(2)
C7 C8 C9 109.2(2)
C11 C9 C8 106.1(2)
C11 C9 C13 127.6(2)
C8 C9 C13 126.3(2)
N1 C10 C11 107.51(18)
N1 C10 C26 107.69(19)
C11 C10 C26 113.35(18)
N1 C10 C12 110.14(16)
C11 C10 C12 107.45(17)
C26 C10 C12 110.65(18)
C9 C11 N2 107.80(19)
C9 C11 C10 134.0(2)
N2 C11 C10 118.22(18)
O1 C12 O2 123.2(2)
O1 C12 C10 124.84(19)
O2 C12 C10 111.98(17)
C18 C13 C14 117.5(3)
C18 C13 C9 121.1(2)
C14 C13 C9 121.3(2)
C15 C14 C13 121.2(3)
C16 C15 C14 119.9(3)
C15 C16 C17 120.5(3)
C15 C16 Cl1 119.9(3)
C17 C16 Cl1 119.5(3)
C16 C17 C18 119.5(3)
C13 C18 C17 121.4(3)
O2 C19 C20 108.14(19)
C25 C20 C21 119.9(3)
C25 C20 C19 121.2(3)
C21 C20 C19 118.9(3)
C20 C21 C22 119.7(3)
C23 C22 C21 120.4(4)
C22 C23 C24 120.9(3)
C23 C24 C25 119.6(4)
C20 C25 C24 119.5(3)
C1 N1 C10 119.84(19)
C7 N2 C11 108.99(18)
C7 N2 C6 127.75(19)
C11 N2 C6 123.16(18)
C12 O2 C19 116.07(17)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C1 C6 1.391(3)
C1 N1 1.392(3)
C1 C2 1.396(3)
C2 C3 1.371(4)
C3 C4 1.374(4)
C4 C5 1.385(4)
C5 C6 1.381(3)
C6 N2 1.416(3)
C7 C8 1.350(3)
C7 N2 1.372(3)
C8 C9 1.416(3)
C9 C11 1.384(3)
C9 C13 1.479(3)
C10 N1 1.458(3)
C10 C11 1.510(3)
C10 C26 1.526(3)
C10 C12 1.543(3)
C11 N2 1.385(3)
C12 O1 1.198(2)
C12 O2 1.324(3)
C13 C18 1.380(4)
C13 C14 1.384(4)
C14 C15 1.378(5)
C15 C16 1.360(5)
C16 C17 1.367(5)
C16 Cl1 1.739(3)
C17 C18 1.381(5)
C19 O2 1.458(3)
C19 C20 1.491(3)
C20 C25 1.372(4)
C20 C21 1.377(4)
C21 C22 1.383(5)
C22 C23 1.350(6)
C23 C24 1.360(5)
C24 C25 1.399(4)
