#------------------------------------------------------------------------------
#$Date: 2019-11-26 14:19:06 +0200 (Tue, 26 Nov 2019) $
#$Revision: 243492 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/55/61/1556133.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_1556133
loop_
_publ_author_name
'Balandier, Jean-Yves'
'Henry, Nicolas'
'Arlin, Jean-Baptiste'
'Sanguinet, Lionel'
'Lemaur, Vincent'
'Niebel, Claude'
'Chattopadhyay, Basab'
'Kennedy, Alan Robert'
'Leriche, Philippe'
'Blanchard, Philippe'
'Cornil, Jérôme'
'Geerts, Yves Henri'
_publ_section_title
;
 Synthesis and characterization of isomerically pure anti- and
 syn-anthradiindole derivatives.
;
_journal_issue                   2
_journal_name_full               'Organic letters'
_journal_page_first              302
_journal_page_last               305
_journal_paper_doi               10.1021/ol303214j
_journal_volume                  15
_journal_year                    2013
_chemical_formula_moiety         'C42 H46 N2 O2'
_chemical_formula_sum            'C42 H46 N2 O2'
_chemical_formula_weight         610.81
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_audit_update_record
;
2012-10-25 # Formatted by publCIF
;
_cell_angle_alpha                101.869(10)
_cell_angle_beta                 94.696(5)
_cell_angle_gamma                114.24(2)
_cell_formula_units_Z            1
_cell_length_a                   8.2943(10)
_cell_length_b                   8.331(9)
_cell_length_c                   13.551(14)
_cell_measurement_reflns_used    1851
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      27.5
_cell_measurement_theta_min      2.7
_cell_volume                     820.9(12)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      100(2)
_diffrn_detector                 CCD
_diffrn_detector_area_resol_mean 28.5714
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_device
;
AFC12 (Right): Kappa 3 circle
;
_diffrn_measurement_device_type
;
Rigaku Saturn724+ (2x2 bin mode)
;
_diffrn_measurement_method       'profile data from ω-scans'
_diffrn_measurement_specimen_support Mitegen
_diffrn_radiation_monochromator  Confocal
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71075
_diffrn_reflns_av_R_equivalents  0.0382
_diffrn_reflns_av_sigmaI/netI    0.0527
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            8234
_diffrn_reflns_theta_full        27.00
_diffrn_reflns_theta_max         27.00
_diffrn_reflns_theta_min         3.13
_diffrn_source                   'Rotating Anode'
_exptl_absorpt_coefficient_mu    0.075
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.878
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.34.40 (release 27-08-2010 CrysAlis171 .NET)
(compiled Aug 27 2010,11:50:40)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            Orange
_exptl_crystal_density_diffrn    1.236
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             328
_exptl_crystal_size_max          0.09
_exptl_crystal_size_mid          0.06
_exptl_crystal_size_min          0.01
_refine_diff_density_max         0.319
_refine_diff_density_min         -0.231
_refine_diff_density_rms         0.052
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.133
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     209
_refine_ls_number_reflns         3574
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.133
_refine_ls_R_factor_all          0.0899
_refine_ls_R_factor_gt           0.0726
_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)+(0.0665P)²+0.3431P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1622
_refine_ls_wR_factor_ref         0.1737
_reflns_number_gt                2921
_reflns_number_total             3574
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            ol303214j_si_002.cif
_cod_data_source_block           2012ncs0733
_cod_original_sg_symbol_H-M      P-1
_cod_database_code               1556133
loop_
_symmetry_equiv_pos_as_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
O1 O 0.80950(19) 0.63554(18) 0.46995(12) 0.0310(4) Uani 1 1 d .
N1 N 0.5956(2) 1.2558(2) 0.66590(13) 0.0240(4) Uani 1 1 d .
C1 C 0.8977(3) 0.8025(3) 0.48477(16) 0.0235(4) Uani 1 1 d .
C2 C 0.8279(3) 0.9303(3) 0.53325(15) 0.0229(4) Uani 1 1 d .
C3 C 0.6627(3) 0.8599(3) 0.56446(16) 0.0235(4) Uani 1 1 d .
H3 H 0.5972 0.7320 0.5547 0.028 Uiso 1 1 calc R
C4 C 0.5941(2) 0.9777(3) 0.60993(16) 0.0220(4) Uani 1 1 d .
C5 C 0.6919(3) 1.1688(3) 0.62146(15) 0.0225(4) Uani 1 1 d .
C6 C 0.8574(3) 1.2413(3) 0.59071(16) 0.0244(5) Uani 1 1 d .
H6 H 0.9222 1.3689 0.5992 0.029 Uiso 1 1 calc R
C7 C 0.9252(3) 1.1211(3) 0.54712(15) 0.0224(4) Uani 1 1 d .
C8 C 0.4393(3) 1.1251(3) 0.68492(16) 0.0234(4) Uani 1 1 d .
C9 C 0.4336(3) 0.9513(3) 0.65209(15) 0.0226(4) Uani 1 1 d .
C10 C 0.2873(3) 0.7984(3) 0.66297(16) 0.0254(5) Uani 1 1 d .
H10 H 0.2800 0.6795 0.6397 0.030 Uiso 1 1 calc R
C11 C 0.1533(3) 0.8244(3) 0.70845(17) 0.0293(5) Uani 1 1 d .
H11 H 0.0542 0.7222 0.7177 0.035 Uiso 1 1 calc R
C12 C 0.1613(3) 0.9988(3) 0.74101(17) 0.0290(5) Uani 1 1 d .
H12 H 0.0673 1.0123 0.7719 0.035 Uiso 1 1 calc R
C13 C 0.3033(3) 1.1524(3) 0.72922(17) 0.0272(5) Uani 1 1 d .
H13 H 0.3077 1.2704 0.7503 0.033 Uiso 1 1 calc R
C14 C 0.6298(3) 1.4459(3) 0.67768(16) 0.0249(5) Uani 1 1 d .
H14A H 0.5182 1.4488 0.6481 0.030 Uiso 1 1 calc R
H14B H 0.7230 1.5005 0.6376 0.030 Uiso 1 1 calc R
C15 C 0.6913(3) 1.5625(3) 0.78793(16) 0.0263(5) Uani 1 1 d .
H15A H 0.8152 1.5830 0.8136 0.032 Uiso 1 1 calc R
H15B H 0.6116 1.4977 0.8316 0.032 Uiso 1 1 calc R
C16 C 0.6868(3) 1.7454(3) 0.79501(16) 0.0267(5) Uani 1 1 d .
H16A H 0.5632 1.7220 0.7662 0.032 Uiso 1 1 calc R
H16B H 0.7677 1.8084 0.7513 0.032 Uiso 1 1 calc R
C17 C 0.7414(3) 1.8735(3) 0.90253(17) 0.0304(5) Uani 1 1 d .
H17A H 0.6640 1.8107 0.9477 0.037 Uiso 1 1 calc R
H17B H 0.8674 1.9039 0.9307 0.037 Uiso 1 1 calc R
C18 C 0.7249(3) 2.0486(3) 0.90283(17) 0.0318(5) Uani 1 1 d .
H18A H 0.5998 2.0164 0.8717 0.038 Uiso 1 1 calc R
H18B H 0.8048 2.1116 0.8587 0.038 Uiso 1 1 calc R
C19 C 0.7717(3) 2.1813(3) 1.00834(18) 0.0326(5) Uani 1 1 d .
H19A H 0.6935 2.1189 1.0533 0.039 Uiso 1 1 calc R
H19B H 0.8979 2.2173 1.0392 0.039 Uiso 1 1 calc R
C20 C 0.7489(3) 2.3515(3) 1.00406(19) 0.0364(6) Uani 1 1 d .
H20A H 0.6229 2.3148 0.9723 0.044 Uiso 1 1 calc R
H20B H 0.8277 2.4138 0.9593 0.044 Uiso 1 1 calc R
C21 C 0.7931(4) 2.4861(3) 1.1088(2) 0.0463(7) Uani 1 1 d .
H21A H 0.7124 2.4273 1.1528 0.069 Uiso 1 1 calc R
H21B H 0.7772 2.5930 1.1003 0.069 Uiso 1 1 calc R
H21C H 0.9181 2.5246 1.1406 0.069 Uiso 1 1 calc R
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
O O 0.0106 0.0060 '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'
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'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_3
C5 N1 C8 108.46(17) .
C5 N1 C14 127.60(17) .
C8 N1 C14 123.28(17) .
O1 C1 C2 120.86(19) .
O1 C1 C7 120.85(18) 2_776
C2 C1 C7 118.28(17) 2_776
C3 C2 C7 120.22(18) .
C3 C2 C1 118.65(18) .
C7 C2 C1 121.13(18) .
C4 C3 C2 119.64(18) .
C4 C3 H3 120.2 .
C2 C3 H3 120.2 .
C3 C4 C5 119.46(19) .
C3 C4 C9 133.66(18) .
C5 C4 C9 106.88(17) .
N1 C5 C6 129.78(18) .
N1 C5 C4 108.71(18) .
C6 C5 C4 121.51(18) .
C5 C6 C7 118.03(18) .
C5 C6 H6 121.0 .
C7 C6 H6 121.0 .
C6 C7 C2 121.12(19) .
C6 C7 C1 118.30(18) 2_776
C2 C7 C1 120.58(18) 2_776
N1 C8 C13 127.95(19) .
N1 C8 C9 109.73(18) .
C13 C8 C9 122.32(18) .
C10 C9 C8 119.72(19) .
C10 C9 C4 134.07(19) .
C8 C9 C4 106.20(17) .
C11 C10 C9 118.39(19) .
C11 C10 H10 120.8 .
C9 C10 H10 120.8 .
C10 C11 C12 121.12(19) .
C10 C11 H11 119.4 .
C12 C11 H11 119.4 .
C13 C12 C11 121.6(2) .
C13 C12 H12 119.2 .
C11 C12 H12 119.2 .
C12 C13 C8 116.82(19) .
C12 C13 H13 121.6 .
C8 C13 H13 121.6 .
N1 C14 C15 114.41(17) .
N1 C14 H14A 108.7 .
C15 C14 H14A 108.7 .
N1 C14 H14B 108.7 .
C15 C14 H14B 108.7 .
H14A C14 H14B 107.6 .
C14 C15 C16 110.60(18) .
C14 C15 H15A 109.5 .
C16 C15 H15A 109.5 .
C14 C15 H15B 109.5 .
C16 C15 H15B 109.5 .
H15A C15 H15B 108.1 .
C15 C16 C17 115.68(19) .
C15 C16 H16A 108.4 .
C17 C16 H16A 108.4 .
C15 C16 H16B 108.4 .
C17 C16 H16B 108.4 .
H16A C16 H16B 107.4 .
C18 C17 C16 112.02(19) .
C18 C17 H17A 109.2 .
C16 C17 H17A 109.2 .
C18 C17 H17B 109.2 .
C16 C17 H17B 109.2 .
H17A C17 H17B 107.9 .
C17 C18 C19 115.1(2) .
C17 C18 H18A 108.5 .
C19 C18 H18A 108.5 .
C17 C18 H18B 108.5 .
C19 C18 H18B 108.5 .
H18A C18 H18B 107.5 .
C20 C19 C18 112.7(2) .
C20 C19 H19A 109.1 .
C18 C19 H19A 109.1 .
C20 C19 H19B 109.1 .
C18 C19 H19B 109.1 .
H19A C19 H19B 107.8 .
C19 C20 C21 113.8(2) .
C19 C20 H20A 108.8 .
C21 C20 H20A 108.8 .
C19 C20 H20B 108.8 .
C21 C20 H20B 108.8 .
H20A C20 H20B 107.7 .
C20 C21 H21A 109.5 .
C20 C21 H21B 109.5 .
H21A C21 H21B 109.5 .
C20 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
_geom_bond_site_symmetry_2
O1 C1 1.239(3) .
N1 C5 1.378(3) .
N1 C8 1.394(3) .
N1 C14 1.461(3) .
C1 C2 1.477(3) .
C1 C7 1.483(3) 2_776
C2 C3 1.392(3) .
C2 C7 1.418(3) .
C3 C4 1.391(3) .
C3 H3 0.9500 .
C4 C5 1.426(3) .
C4 C9 1.443(3) .
C5 C6 1.393(3) .
C6 C7 1.393(3) .
C6 H6 0.9500 .
C7 C1 1.483(3) 2_776
C8 C13 1.396(3) .
C8 C9 1.405(3) .
C9 C10 1.398(3) .
C10 C11 1.385(3) .
C10 H10 0.9500 .
C11 C12 1.401(3) .
C11 H11 0.9500 .
C12 C13 1.388(3) .
C12 H12 0.9500 .
C13 H13 0.9500 .
C14 C15 1.519(3) .
C14 H14A 0.9900 .
C14 H14B 0.9900 .
C15 C16 1.523(3) .
C15 H15A 0.9900 .
C15 H15B 0.9900 .
C16 C17 1.524(3) .
C16 H16A 0.9900 .
C16 H16B 0.9900 .
C17 C18 1.519(3) .
C17 H17A 0.9900 .
C17 H17B 0.9900 .
C18 C19 1.525(3) .
C18 H18A 0.9900 .
C18 H18B 0.9900 .
C19 C20 1.517(3) .
C19 H19A 0.9900 .
C19 H19B 0.9900 .
C20 C21 1.526(4) .
C20 H20A 0.9900 .
C20 H20B 0.9900 .
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
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_4
O1 C1 C2 C3 1.6(3) . .
C7 C1 C2 C3 -179.29(18) 2_776 .
O1 C1 C2 C7 -177.75(19) . .
C7 C1 C2 C7 1.3(3) 2_776 .
C7 C2 C3 C4 -0.4(3) . .
C1 C2 C3 C4 -179.77(19) . .
C2 C3 C4 C5 1.7(3) . .
C2 C3 C4 C9 -178.3(2) . .
C8 N1 C5 C6 -178.6(2) . .
C14 N1 C5 C6 10.6(4) . .
C8 N1 C5 C4 1.0(2) . .
C14 N1 C5 C4 -169.82(19) . .
C3 C4 C5 N1 178.60(18) . .
C9 C4 C5 N1 -1.4(2) . .
C3 C4 C5 C6 -1.8(3) . .
C9 C4 C5 C6 178.23(18) . .
N1 C5 C6 C7 -179.9(2) . .
C4 C5 C6 C7 0.6(3) . .
C5 C6 C7 C2 0.7(3) . .
C5 C6 C7 C1 -179.36(18) . 2_776
C3 C2 C7 C6 -0.8(3) . .
C1 C2 C7 C6 178.51(19) . .
C3 C2 C7 C1 179.27(18) . 2_776
C1 C2 C7 C1 -1.4(3) . 2_776
C5 N1 C8 C13 179.9(2) . .
C14 N1 C8 C13 -8.8(3) . .
C5 N1 C8 C9 -0.2(2) . .
C14 N1 C8 C9 171.09(18) . .
N1 C8 C9 C10 -179.52(18) . .
C13 C8 C9 C10 0.4(3) . .
N1 C8 C9 C4 -0.6(2) . .
C13 C8 C9 C4 179.28(19) . .
C3 C4 C9 C10 -0.1(4) . .
C5 C4 C9 C10 179.9(2) . .
C3 C4 C9 C8 -178.8(2) . .
C5 C4 C9 C8 1.2(2) . .
C8 C9 C10 C11 -1.5(3) . .
C4 C9 C10 C11 -180.0(2) . .
C9 C10 C11 C12 1.3(3) . .
C10 C11 C12 C13 0.0(3) . .
C11 C12 C13 C8 -1.0(3) . .
N1 C8 C13 C12 -179.2(2) . .
C9 C8 C13 C12 0.9(3) . .
C5 N1 C14 C15 -112.0(2) . .
C8 N1 C14 C15 78.4(2) . .
N1 C14 C15 C16 -168.50(16) . .
C14 C15 C16 C17 178.59(17) . .
C15 C16 C17 C18 -177.44(18) . .
C16 C17 C18 C19 178.15(18) . .
C17 C18 C19 C20 -178.75(19) . .
C18 C19 C20 C21 179.5(2) . .
