#------------------------------------------------------------------------------
#$Date: 2025-08-18 16:30:32 +0300 (Mon, 18 Aug 2025) $
#$Revision: 301775 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/50/71/1507172.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_1507172
loop_
_publ_author_name
'Kelgtermans, Hans'
'Dobrzańska, Liliana'
'Meervelt, Luc Van'
'Dehaen, Wim'
_publ_section_title
;
 Synthesis of Functionalized Dioxa-aza[7]helicenes Using Palladium
 Catalyzed Arylations.
;
_journal_issue                   6
_journal_name_full               'Organic letters'
_journal_page_first              1500
_journal_page_last               1503
_journal_paper_doi               10.1021/ol300236t
_journal_volume                  14
_journal_year                    2012
_chemical_formula_moiety         'C30 H17 N O2'
_chemical_formula_sum            'C30 H17 N O2'
_chemical_formula_weight         423.45
_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                79.838(4)
_cell_angle_beta                 83.351(4)
_cell_angle_gamma                74.729(4)
_cell_formula_units_Z            2
_cell_length_a                   8.3210(5)
_cell_length_b                   9.3857(6)
_cell_length_c                   13.8217(7)
_cell_measurement_reflns_used    1753
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      70.73
_cell_measurement_theta_min      3.257
_cell_volume                     1022.27(11)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      298(2)
_diffrn_measured_fraction_theta_full 0.976
_diffrn_measured_fraction_theta_max 0.953
_diffrn_measurement_device_type  'Bruker SMART 6000'
_diffrn_measurement_method       'ω and φ'
_diffrn_radiation_monochromator  'crossed G\"obel mirrors'
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0446
_diffrn_reflns_av_sigmaI/netI    0.0596
_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       -7
_diffrn_reflns_number            4530
_diffrn_reflns_theta_full        68.00
_diffrn_reflns_theta_max         70.84
_diffrn_reflns_theta_min         3.26
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.683
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.376
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             440
_exptl_crystal_size_max          0.21
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.09
_refine_diff_density_max         0.202
_refine_diff_density_min         -0.259
_refine_diff_density_rms         0.053
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.895
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     298
_refine_ls_number_reflns         3753
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.895
_refine_ls_R_factor_all          0.0636
_refine_ls_R_factor_gt           0.0460
_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)+(0.0624P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1064
_refine_ls_wR_factor_ref         0.1140
_reflns_number_gt                2539
_reflns_number_total             3753
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol300236t_si_001.cif
_cod_data_source_block           I
_cod_original_cell_volume        1022.27(10)
_cod_database_code               1507172
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
N1 N 0.71620(18) 0.01900(16) 0.59923(10) 0.0454(4) Uani 1 1 d .
C2 C 0.6309(2) 0.1239(2) 0.52627(13) 0.0426(4) Uani 1 1 d .
C3 C 0.6925(2) 0.08008(19) 0.43345(12) 0.0402(4) Uani 1 1 d .
C4 C 0.8090(2) -0.06356(19) 0.45210(12) 0.0397(4) Uani 1 1 d .
C5 C 0.8294(2) -0.09217(19) 0.55435(13) 0.0420(4) Uani 1 1 d .
C6 C 0.5045(2) 0.2527(2) 0.53818(14) 0.0498(5) Uani 1 1 d .
H6 H 0.4621 0.2734 0.6008 0.060 Uiso 1 1 calc R
C7 C 0.4439(2) 0.3480(2) 0.45605(14) 0.0532(5) Uani 1 1 d .
H7 H 0.3570 0.4326 0.4613 0.064 Uiso 1 1 calc R
C8 C 0.5169(2) 0.3138(2) 0.36502(14) 0.0478(4) Uani 1 1 d .
C9 C 0.6428(2) 0.1874(2) 0.34952(13) 0.0428(4) Uani 1 1 d .
O10 O 0.48162(16) 0.41243(14) 0.27736(10) 0.0562(4) Uani 1 1 d .
C11 C 0.5971(2) 0.3499(2) 0.20743(14) 0.0498(5) Uani 1 1 d .
C12 C 0.7010(2) 0.2139(2) 0.24632(13) 0.0445(4) Uani 1 1 d .
C13 C 0.6130(3) 0.4176(2) 0.11084(15) 0.0596(5) Uani 1 1 d .
H13 H 0.5396 0.5070 0.0870 0.071 Uiso 1 1 calc R
C14 C 0.7431(3) 0.3463(2) 0.05152(15) 0.0616(6) Uani 1 1 d .
H14 H 0.7570 0.3875 -0.0143 0.074 Uiso 1 1 calc R
C15 C 0.8544(3) 0.2134(2) 0.08838(14) 0.0574(5) Uani 1 1 d .
H15 H 0.9429 0.1689 0.0472 0.069 Uiso 1 1 calc R
C16 C 0.8350(2) 0.1469(2) 0.18505(14) 0.0500(5) Uani 1 1 d .
H16 H 0.9101 0.0587 0.2091 0.060 Uiso 1 1 calc R
C17 C 0.8952(2) -0.17775(19) 0.39697(12) 0.0409(4) Uani 1 1 d .
C18 C 1.0150(2) -0.2945(2) 0.44454(13) 0.0452(4) Uani 1 1 d .
C19 C 1.0498(2) -0.3115(2) 0.54227(14) 0.0497(5) Uani 1 1 d .
H19 H 1.1364 -0.3884 0.5685 0.060 Uiso 1 1 calc R
C20 C 0.9513(2) -0.2102(2) 0.59877(14) 0.0479(4) Uani 1 1 d .
H20 H 0.9657 -0.2203 0.6656 0.058 Uiso 1 1 calc R
C21 C 0.8825(2) -0.22322(19) 0.30332(13) 0.0433(4) Uani 1 1 d .
C22 C 1.0037(2) -0.3573(2) 0.30014(14) 0.0483(4) Uani 1 1 d .
O23 O 1.08937(16) -0.40153(14) 0.38423(10) 0.0521(3) Uani 1 1 d .
C24 C 0.7728(2) -0.1740(2) 0.22860(13) 0.0502(5) Uani 1 1 d .
H24 H 0.6870 -0.0876 0.2298 0.060 Uiso 1 1 calc R
C25 C 0.7947(3) -0.2573(2) 0.15237(15) 0.0617(6) Uani 1 1 d .
H25 H 0.7226 -0.2255 0.1019 0.074 Uiso 1 1 calc R
C26 C 0.9217(3) -0.3870(2) 0.14970(16) 0.0641(6) Uani 1 1 d .
H26 H 0.9344 -0.4390 0.0968 0.077 Uiso 1 1 calc R
C27 C 1.0293(3) -0.4402(2) 0.22400(15) 0.0592(5) Uani 1 1 d .
H27 H 1.1145 -0.5271 0.2229 0.071 Uiso 1 1 calc R
C28 C 0.6978(2) 0.0245(2) 0.70227(13) 0.0454(4) Uani 1 1 d .
C29 C 0.6755(2) -0.0996(2) 0.76797(14) 0.0527(5) Uani 1 1 d .
H29 H 0.6684 -0.1847 0.7447 0.063 Uiso 1 1 calc R
C30 C 0.6639(3) -0.0967(3) 0.86804(15) 0.0659(6) Uani 1 1 d .
H30 H 0.6505 -0.1806 0.9121 0.079 Uiso 1 1 calc R
C31 C 0.6720(3) 0.0302(3) 0.90326(16) 0.0726(7) Uani 1 1 d .
H31 H 0.6643 0.0319 0.9707 0.087 Uiso 1 1 calc R
C32 C 0.6914(3) 0.1532(3) 0.83770(16) 0.0672(6) Uani 1 1 d .
H32 H 0.6963 0.2390 0.8610 0.081 Uiso 1 1 calc R
C33 C 0.7037(2) 0.1515(2) 0.73729(15) 0.0556(5) Uani 1 1 d .
H33 H 0.7159 0.2360 0.6934 0.067 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
C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 '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
C5 N1 C2 108.42(14)
C5 N1 C28 124.71(15)
C2 N1 C28 126.83(15)
N1 C2 C6 127.87(16)
N1 C2 C3 108.69(15)
C6 C2 C3 123.44(16)
C2 C3 C9 116.39(16)
C2 C3 C4 106.89(15)
C9 C3 C4 136.29(16)
C5 C4 C17 116.60(15)
C5 C4 C3 106.51(15)
C17 C4 C3 136.81(16)
N1 C5 C20 127.43(16)
N1 C5 C4 108.95(15)
C20 C5 C4 123.55(17)
C7 C6 C2 118.98(17)
C6 C7 C8 117.63(18)
C7 C8 C9 125.42(17)
C7 C8 O10 122.58(17)
C9 C8 O10 111.74(16)
C8 C9 C3 117.11(16)
C8 C9 C12 105.48(15)
C3 C9 C12 136.96(17)
C11 O10 C8 104.80(14)
O10 C11 C13 123.62(18)
O10 C11 C12 112.30(16)
C13 C11 C12 124.02(19)
C11 C12 C16 117.73(17)
C11 C12 C9 105.45(16)
C16 C12 C9 136.51(17)
C14 C13 C11 116.74(19)
C13 C14 C15 121.20(19)
C16 C15 C14 121.0(2)
C15 C16 C12 119.17(18)
C18 C17 C4 116.77(16)
C18 C17 C21 105.03(15)
C4 C17 C21 137.63(16)
C19 C18 O23 122.45(16)
C19 C18 C17 125.52(17)
O23 C18 C17 111.85(16)
C20 C19 C18 117.31(17)
C19 C20 C5 118.97(17)
C24 C21 C22 118.32(17)
C24 C21 C17 135.55(17)
C22 C21 C17 105.69(16)
O23 C22 C27 123.78(18)
O23 C22 C21 112.07(16)
C27 C22 C21 124.08(19)
C22 O23 C18 105.03(14)
C25 C24 C21 118.33(18)
C24 C25 C26 121.6(2)
C27 C26 C25 121.3(2)
C26 C27 C22 116.33(19)
C33 C28 C29 119.71(18)
C33 C28 N1 120.62(17)
C29 C28 N1 119.67(17)
C30 C29 C28 119.9(2)
C29 C30 C31 120.4(2)
C32 C31 C30 119.3(2)
C31 C32 C33 120.8(2)
C28 C33 C32 119.9(2)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
N1 C5 1.392(2)
N1 C2 1.392(2)
N1 C28 1.423(2)
C2 C6 1.399(2)
C2 C3 1.414(2)
C3 C9 1.418(2)
C3 C4 1.439(2)
C4 C5 1.413(2)
C4 C17 1.414(2)
C5 C20 1.395(2)
C6 C7 1.371(3)
C7 C8 1.385(3)
C8 C9 1.391(2)
C8 O10 1.398(2)
C9 C12 1.452(2)
O10 C11 1.375(2)
C11 C13 1.381(3)
C11 C12 1.396(2)
C12 C16 1.399(2)
C13 C14 1.378(3)
C14 C15 1.396(3)
C15 C16 1.382(3)
C17 C18 1.396(2)
C17 C21 1.456(2)
C18 C19 1.387(3)
C18 O23 1.391(2)
C19 C20 1.374(3)
C21 C24 1.393(2)
C21 C22 1.394(2)
C22 O23 1.377(2)
C22 C27 1.381(3)
C24 C25 1.387(3)
C25 C26 1.389(3)
C26 C27 1.379(3)
C28 C33 1.378(3)
C28 C29 1.385(2)
C29 C30 1.380(3)
C30 C31 1.384(3)
C31 C32 1.370(3)
C32 C33 1.382(3)
loop_
_cod_related_entry_id
_cod_related_entry_code
_cod_related_entry_database
1 30651799 ChemSpider
2 139039951 PubChem
