#------------------------------------------------------------------------------
#$Date: 2017-10-14 22:27:35 +0300 (Sat, 14 Oct 2017) $
#$Revision: 202017 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/10/46/7104661.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_7104661
loop_
_publ_author_name
'Pieters, Grégory'
'Gaucher, Anne'
'Prim, Damien'
'Marrot, Jérôme'
_publ_section_title
;
 First expeditious synthesis of 6,11-diamino-[6]carbohelicenes.
;
_journal_issue                   32
_journal_name_full
'Chemical communications (Cambridge, England)'
_journal_page_first              4827
_journal_page_last               4828
_journal_paper_doi               10.1039/b905670j
_journal_volume                  34
_journal_year                    2009
_chemical_formula_sum            'C34 H29 N3 O4'
_chemical_formula_weight         543.60
_chemical_name_systematic
;
?
;
_space_group_IT_number           2
_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
_cell_angle_alpha                79.913(7)
_cell_angle_beta                 75.844(7)
_cell_angle_gamma                73.560(7)
_cell_formula_units_Z            2
_cell_length_a                   9.4922(14)
_cell_length_b                   11.5758(16)
_cell_length_c                   13.5860(18)
_cell_measurement_reflns_used    9837
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      30.04
_cell_measurement_theta_min      2.28
_cell_volume                     1379.3(3)
_computing_cell_refinement       'Bruker APEX2'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean 512x512
_diffrn_measured_fraction_theta_full 0.982
_diffrn_measured_fraction_theta_max 0.982
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_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  0.0345
_diffrn_reflns_av_sigmaI/netI    0.0320
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            40142
_diffrn_reflns_theta_full        30.17
_diffrn_reflns_theta_max         30.17
_diffrn_reflns_theta_min         1.56
_exptl_absorpt_coefficient_mu    0.087
_exptl_absorpt_correction_T_max  0.9948
_exptl_absorpt_correction_T_min  0.9795
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Sheldrick, V2.10)'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.309
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       parallelepiped
_exptl_crystal_F_000             572
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.06
_refine_diff_density_max         0.447
_refine_diff_density_min         -0.212
_refine_diff_density_rms         0.060
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.062
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     375
_refine_ls_number_reflns         8030
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.062
_refine_ls_R_factor_all          0.0630
_refine_ls_R_factor_gt           0.0469
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0711P)²+0.4968P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1267
_refine_ls_wR_factor_ref         0.1397
_reflns_number_gt                6310
_reflns_number_total             8030
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            b905670j.txt
_cod_data_source_block           1
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic'
according to '/home/saulius/struct/CIF-dictionaries/cif_core.dic'
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_enum 1527 2010-12-29 10:47:43Z saulius 
;
_cod_original_sg_symbol_H-M      P-1
_cod_database_code               7104661
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
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.55184(10) 1.38456(8) 0.14173(8) 0.0207(2) Uani 1 1 d . . .
O2 O 1.06853(11) 0.33379(9) 0.11887(9) 0.0280(2) Uani 1 1 d . . .
O3 O 0.28330(11) 0.86666(9) 0.30663(8) 0.0225(2) Uani 1 1 d . . .
O4 O 0.65116(11) 0.59618(9) 0.60970(7) 0.0223(2) Uani 1 1 d . . .
N1 N 0.78132(12) 1.27404(9) 0.17044(8) 0.0161(2) Uani 1 1 d . . .
H1' H 0.8702 1.2797 0.1746 0.019 Uiso 1 1 calc R . .
N2 N 1.23667(12) 0.40102(9) 0.17109(8) 0.0160(2) Uani 1 1 d . . .
H2' H 1.3320 0.3914 0.1711 0.019 Uiso 1 1 calc R . .
N3 N 0.92194(19) 0.19907(14) 0.40550(14) 0.0448(4) Uani 1 1 d . . .
C1 C 0.68345(15) 0.80842(11) 0.21098(10) 0.0168(2) Uani 1 1 d . . .
H1 H 0.7627 0.7416 0.1878 0.020 Uiso 1 1 calc R . .
C2 C 0.53939(15) 0.79601(12) 0.23856(10) 0.0189(3) Uani 1 1 d . . .
H2 H 0.5198 0.7215 0.2332 0.023 Uiso 1 1 calc R . .
C3 C 0.41979(14) 0.89283(12) 0.27490(10) 0.0178(2) Uani 1 1 d . . .
C4 C 0.44652(14) 1.00363(12) 0.27540(10) 0.0170(2) Uani 1 1 d . . .
H4 H 0.3658 1.0699 0.2978 0.020 Uiso 1 1 calc R . .
C5 C 0.61880(14) 1.13686(11) 0.23264(10) 0.0163(2) Uani 1 1 d . . .
H5 H 0.5383 1.2023 0.2569 0.020 Uiso 1 1 calc R . .
C6 C 0.75668(14) 1.15642(11) 0.18864(9) 0.0150(2) Uani 1 1 d . . .
C7 C 1.02364(14) 1.07694(11) 0.10259(10) 0.0161(2) Uani 1 1 d . . .
H7 H 1.0350 1.1574 0.0849 0.019 Uiso 1 1 calc R . .
C8 C 1.13996(14) 0.98200(11) 0.07170(10) 0.0162(2) Uani 1 1 d . . .
H8 H 1.2272 0.9970 0.0252 0.019 Uiso 1 1 calc R . .
C9 C 1.25434(14) 0.76325(12) 0.07273(10) 0.0178(2) Uani 1 1 d . . .
H9 H 1.3411 0.7801 0.0268 0.021 Uiso 1 1 calc R . .
C10 C 1.24806(14) 0.64636(11) 0.10392(10) 0.0174(2) Uani 1 1 d . . .
H10 H 1.3230 0.5824 0.0723 0.021 Uiso 1 1 calc R . .
C11 C 1.12727(14) 0.49629(11) 0.22261(10) 0.0158(2) Uani 1 1 d . . .
C12 C 1.02395(14) 0.46835(11) 0.30498(10) 0.0174(2) Uani 1 1 d . . .
H12 H 1.0191 0.3865 0.3249 0.021 Uiso 1 1 calc R . .
C13 C 0.82877(15) 0.52973(12) 0.45573(10) 0.0181(2) Uani 1 1 d . . .
H13 H 0.8249 0.4476 0.4757 0.022 Uiso 1 1 calc R . .
C14 C 0.74419(15) 0.61705(12) 0.51741(10) 0.0183(2) Uani 1 1 d . . .
C15 C 0.75273(15) 0.73870(12) 0.48867(10) 0.0184(2) Uani 1 1 d . . .
H15 H 0.6995 0.7982 0.5336 0.022 Uiso 1 1 calc R . .
C16 C 0.83770(14) 0.77124(11) 0.39601(10) 0.0162(2) Uani 1 1 d . . .
H16 H 0.8403 0.8537 0.3773 0.019 Uiso 1 1 calc R . .
C4A C 0.59456(14) 1.01880(11) 0.24250(9) 0.0152(2) Uani 1 1 d . . .
C6A C 0.88460(14) 1.05613(11) 0.16147(9) 0.0144(2) Uani 1 1 d . . .
C8A C 1.13250(14) 0.86056(11) 0.10812(9) 0.0152(2) Uani 1 1 d . . .
C10A C 1.12929(14) 0.61959(11) 0.18392(9) 0.0153(2) Uani 1 1 d . . .
C12A C 0.92228(14) 0.56199(11) 0.36189(9) 0.0156(2) Uani 1 1 d . . .
C16A C 0.92173(14) 0.68488(11) 0.32756(9) 0.0145(2) Uani 1 1 d . . .
C16B C 1.01421(13) 0.71480(11) 0.22917(9) 0.0140(2) Uani 1 1 d . . .
C16C C 1.00275(14) 0.83686(11) 0.17689(9) 0.0140(2) Uani 1 1 d . . .
C16D C 0.86821(14) 0.93598(11) 0.18830(9) 0.0138(2) Uani 1 1 d . . .
C16E C 0.71730(14) 0.91887(11) 0.21622(9) 0.0145(2) Uani 1 1 d . . .
C17 C 0.68040(14) 1.37916(11) 0.14715(9) 0.0160(2) Uani 1 1 d . . .
C18 C 0.73913(16) 1.49107(12) 0.12782(12) 0.0239(3) Uani 1 1 d . . .
H18A H 0.6613 1.5619 0.1089 0.036 Uiso 1 1 calc R . .
H18B H 0.8280 1.4815 0.0721 0.036 Uiso 1 1 calc R . .
H18C H 0.7663 1.5025 0.1899 0.036 Uiso 1 1 calc R . .
C19 C 1.19915(14) 0.32549(11) 0.12258(10) 0.0169(2) Uani 1 1 d . . .
C20 C 1.32760(15) 0.23051(12) 0.07181(11) 0.0198(3) Uani 1 1 d . . .
H20A H 1.3194 0.1499 0.1055 0.030 Uiso 1 1 calc R . .
H20B H 1.4228 0.2436 0.0773 0.030 Uiso 1 1 calc R . .
H20C H 1.3242 0.2362 -0.0004 0.030 Uiso 1 1 calc R . .
C21 C 0.15809(15) 0.96397(14) 0.34029(11) 0.0247(3) Uani 1 1 d . . .
H21A H 0.1762 0.9954 0.3973 0.037 Uiso 1 1 calc R . .
H21B H 0.0670 0.9343 0.3628 0.037 Uiso 1 1 calc R . .
H21C H 0.1452 1.0289 0.2838 0.037 Uiso 1 1 calc R . .
C22 C 0.63435(18) 0.47496(13) 0.63878(11) 0.0262(3) Uani 1 1 d . . .
H22A H 0.5888 0.4535 0.5894 0.039 Uiso 1 1 calc R . .
H22B H 0.5696 0.4697 0.7069 0.039 Uiso 1 1 calc R . .
H22C H 0.7331 0.4188 0.6400 0.039 Uiso 1 1 calc R . .
C23 C 0.6396(2) 0.2070(2) 0.46307(14) 0.0472(5) Uani 1 1 d . . .
H23A H 0.6024 0.2340 0.5313 0.071 Uiso 1 1 calc R . .
H23B H 0.6246 0.1262 0.4651 0.071 Uiso 1 1 calc R . .
H23C H 0.5847 0.2641 0.4147 0.071 Uiso 1 1 calc R . .
C24 C 0.7981(2) 0.20209(15) 0.43066(13) 0.0331(4) 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'
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_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C3 O3 C21 116.65(11) . . ?
C14 O4 C22 116.51(11) . . ?
C17 N1 C6 126.07(11) . . ?
C17 N1 H1' 117.0 . . ?
C6 N1 H1' 117.0 . . ?
C19 N2 C11 122.51(11) . . ?
C19 N2 H2' 118.7 . . ?
C11 N2 H2' 118.7 . . ?
C2 C1 C16E 121.52(12) . . ?
C2 C1 H1 119.2 . . ?
C16E C1 H1 119.2 . . ?
C1 C2 C3 120.55(12) . . ?
C1 C2 H2 119.7 . . ?
C3 C2 H2 119.7 . . ?
O3 C3 C4 125.29(12) . . ?
O3 C3 C2 115.01(11) . . ?
C4 C3 C2 119.69(12) . . ?
C3 C4 C4A 119.97(12) . . ?
C3 C4 H4 120.0 . . ?
C4A C4 H4 120.0 . . ?
C6 C5 C4A 120.46(11) . . ?
C6 C5 H5 119.8 . . ?
C4A C5 H5 119.8 . . ?
C5 C6 N1 121.75(11) . . ?
C5 C6 C6A 120.68(11) . . ?
N1 C6 C6A 117.55(11) . . ?
C8 C7 C6A 120.24(11) . . ?
C8 C7 H7 119.9 . . ?
C6A C7 H7 119.9 . . ?
C7 C8 C8A 120.81(11) . . ?
C7 C8 H8 119.6 . . ?
C8A C8 H8 119.6 . . ?
C10 C9 C8A 120.67(11) . . ?
C10 C9 H9 119.7 . . ?
C8A C9 H9 119.7 . . ?
C9 C10 C10A 120.11(11) . . ?
C9 C10 H10 119.9 . . ?
C10A C10 H10 119.9 . . ?
C12 C11 N2 119.60(11) . . ?
C12 C11 C10A 121.83(11) . . ?
N2 C11 C10A 118.56(11) . . ?
C11 C12 C12A 120.01(11) . . ?
C11 C12 H12 120.0 . . ?
C12A C12 H12 120.0 . . ?
C14 C13 C12A 119.99(11) . . ?
C14 C13 H13 120.0 . . ?
C12A C13 H13 120.0 . . ?
C13 C14 O4 124.96(12) . . ?
C13 C14 C15 119.89(11) . . ?
O4 C14 C15 115.13(11) . . ?
C16 C15 C14 120.29(12) . . ?
C16 C15 H15 119.9 . . ?
C14 C15 H15 119.9 . . ?
C15 C16 C16A 121.72(11) . . ?
C15 C16 H16 119.1 . . ?
C16A C16 H16 119.1 . . ?
C16E C4A C4 120.60(11) . . ?
C16E C4A C5 119.89(11) . . ?
C4 C4A C5 119.48(11) . . ?
C16D C6A C7 119.76(11) . . ?
C16D C6A C6 119.28(11) . . ?
C7 C6A C6 120.84(11) . . ?
C16C C8A C9 120.28(11) . . ?
C16C C8A C8 120.17(11) . . ?
C9 C8A C8 119.52(11) . . ?
C16B C10A C10 120.27(11) . . ?
C16B C10A C11 119.06(11) . . ?
C10 C10A C11 120.63(11) . . ?
C16A C12A C13 120.78(11) . . ?
C16A C12A C12 119.94(11) . . ?
C13 C12A C12 119.18(11) . . ?
C12A C16A C16 116.94(11) . . ?
C12A C16A C16B 119.21(11) . . ?
C16 C16A C16B 123.69(11) . . ?
C10A C16B C16C 117.66(10) . . ?
C10A C16B C16A 117.85(10) . . ?
C16C C16B C16A 124.38(11) . . ?
C8A C16C C16D 117.35(10) . . ?
C8A C16C C16B 117.40(11) . . ?
C16D C16C C16B 125.24(11) . . ?
C6A C16D C16E 117.90(11) . . ?
C6A C16D C16C 118.22(11) . . ?
C16E C16D C16C 123.61(10) . . ?
C4A C16E C1 117.11(11) . . ?
C4A C16E C16D 119.26(11) . . ?
C1 C16E C16D 123.44(11) . . ?
O1 C17 N1 123.68(11) . . ?
O1 C17 C18 121.65(11) . . ?
N1 C17 C18 114.67(11) . . ?
C17 C18 H18A 109.5 . . ?
C17 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
C17 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
O2 C19 N2 122.43(12) . . ?
O2 C19 C20 121.67(12) . . ?
N2 C19 C20 115.90(11) . . ?
C19 C20 H20A 109.5 . . ?
C19 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
C19 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
O3 C21 H21A 109.5 . . ?
O3 C21 H21B 109.5 . . ?
H21A C21 H21B 109.5 . . ?
O3 C21 H21C 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
O4 C22 H22A 109.5 . . ?
O4 C22 H22B 109.5 . . ?
H22A C22 H22B 109.5 . . ?
O4 C22 H22C 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
C24 C23 H23A 109.5 . . ?
C24 C23 H23B 109.5 . . ?
H23A C23 H23B 109.5 . . ?
C24 C23 H23C 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?
N3 C24 C23 179.5(2) . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C17 1.2238(15) . ?
O2 C19 1.2290(16) . ?
O3 C3 1.3636(15) . ?
O3 C21 1.4308(17) . ?
O4 C14 1.3724(15) . ?
O4 C22 1.4326(17) . ?
N1 C17 1.3609(16) . ?
N1 C6 1.4155(15) . ?
N1 H1' 0.8800 . ?
N2 C19 1.3486(16) . ?
N2 C11 1.4322(16) . ?
N2 H2' 0.8800 . ?
N3 C24 1.134(2) . ?
C1 C2 1.3684(18) . ?
C1 C16E 1.4208(17) . ?
C1 H1 0.9500 . ?
C2 C3 1.4101(19) . ?
C2 H2 0.9500 . ?
C3 C4 1.3775(18) . ?
C4 C4A 1.4178(17) . ?
C4 H4 0.9500 . ?
C5 C6 1.3635(17) . ?
C5 C4A 1.4274(17) . ?
C5 H5 0.9500 . ?
C6 C6A 1.4461(17) . ?
C7 C8 1.3606(17) . ?
C7 C6A 1.4269(17) . ?
C7 H7 0.9500 . ?
C8 C8A 1.4219(17) . ?
C8 H8 0.9500 . ?
C9 C10 1.3589(18) . ?
C9 C8A 1.4205(17) . ?
C9 H9 0.9500 . ?
C10 C10A 1.4244(17) . ?
C10 H10 0.9500 . ?
C11 C12 1.3545(18) . ?
C11 C10A 1.4357(17) . ?
C12 C12A 1.4285(17) . ?
C12 H12 0.9500 . ?
C13 C14 1.3699(18) . ?
C13 C12A 1.4214(17) . ?
C13 H13 0.9500 . ?
C14 C15 1.4137(18) . ?
C15 C16 1.3735(17) . ?
C15 H15 0.9500 . ?
C16 C16A 1.4184(17) . ?
C16 H16 0.9500 . ?
C4A C16E 1.4147(17) . ?
C6A C16D 1.4172(16) . ?
C8A C16C 1.4155(17) . ?
C10A C16B 1.4189(17) . ?
C12A C16A 1.4162(17) . ?
C16A C16B 1.4538(16) . ?
C16B C16C 1.4532(16) . ?
C16C C16D 1.4517(17) . ?
C16D C16E 1.4504(17) . ?
C17 C18 1.5086(18) . ?
C18 H18A 0.9800 . ?
C18 H18B 0.9800 . ?
C18 H18C 0.9800 . ?
C19 C20 1.5055(18) . ?
C20 H20A 0.9800 . ?
C20 H20B 0.9800 . ?
C20 H20C 0.9800 . ?
C21 H21A 0.9800 . ?
C21 H21B 0.9800 . ?
C21 H21C 0.9800 . ?
C22 H22A 0.9800 . ?
C22 H22B 0.9800 . ?
C22 H22C 0.9800 . ?
C23 C24 1.448(3) . ?
C23 H23A 0.9800 . ?
C23 H23B 0.9800 . ?
C23 H23C 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
_geom_hbond_site_symmetry_A
N1 H1' O2 0.88 2.08 2.8923(15) 153.7 1_565
N2 H2' O1 0.88 2.01 2.8750(15) 168.4 1_645
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 30653139
