#------------------------------------------------------------------------------
#$Date: 2016-06-10 18:40:11 +0300 (Fri, 10 Jun 2016) $
#$Revision: 183311 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/11/90/7119023.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_7119023
loop_
_publ_author_name
'Ying Xie'
'Xun Chen'
'Xin Liu'
'Shi-Jian Su'
'Jianzhang Li'
'Wei Zeng'
_publ_section_title
;
 Rh(III)-catalyzed relay carbenoid functionalization of aromatic C-H
 bonds: access to pi-conjugated fused heteroarenes
;
_journal_name_full               Chem.Commun.
_journal_page_first              5856
_journal_volume                  52
_journal_year                    2016
_chemical_formula_sum            'C28 H27 N O6'
_chemical_formula_weight         473.51
_chemical_name_common            'fused heterocycle'
_chemical_name_systematic        1-azaphenalene
_chemical_properties_physical    Photo-sensitive
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_audit_update_record
;
2015-12-22 deposited with the CCDC.
2016-03-29 downloaded from the CCDC.
;
_cell_angle_alpha                90.00
_cell_angle_beta                 112.100(5)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   12.3361(5)
_cell_length_b                   16.8521(5)
_cell_length_c                   12.0571(5)
_cell_measurement_temperature    571(2)
_cell_measurement_theta_max      62.71
_cell_measurement_theta_min      4.67
_cell_volume                     2322.38(17)
_computing_cell_refinement       'SMART (Bruker, 1998)'
_computing_data_collection       'SMART (Bruker, 1998)'
_computing_data_reduction        'SAIRT (Bruker, 1998)'
_computing_molecular_graphics    'ORTEP-II (Johnson, 1976)'
_computing_publication_material  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      571(2)
_diffrn_measured_fraction_theta_full 0.979
_diffrn_measured_fraction_theta_max 0.979
_diffrn_measurement_device_type  'SMART (Bruker, 1998)'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0281
_diffrn_reflns_av_sigmaI/netI    0.0246
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            9906
_diffrn_reflns_theta_full        62.77
_diffrn_reflns_theta_max         62.77
_diffrn_reflns_theta_min         4.67
_exptl_absorpt_coefficient_mu    0.781
_exptl_absorpt_correction_T_max  0.8723
_exptl_absorpt_correction_T_min  0.8111
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.354
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plane
_exptl_crystal_F_000             1000
_exptl_crystal_preparation       Luminescent
_exptl_crystal_recrystallization_method 'Vapour Deposition'
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.21
_exptl_crystal_size_min          0.18
_refine_diff_density_max         0.468
_refine_diff_density_min         -0.467
_refine_diff_density_rms         0.053
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.051
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     316
_refine_ls_number_reflns         3646
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.051
_refine_ls_R_factor_all          0.0574
_refine_ls_R_factor_gt           0.0513
_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)+(0.0730P)²+1.7278P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1346
_refine_ls_wR_factor_ref         0.1402
_reflns_number_gt                3200
_reflns_number_total             3646
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c6cc00254d2.cif
_cod_data_source_block           sad
_cod_original_cell_volume        2322.38(15)
_cod_original_sg_symbol_H-M      P21/C
_cod_database_code               7119023
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, 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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.73640(13) -0.19366(10) 0.65160(13) 0.0326(4) Uani 1 1 d . . .
O2 O 0.65120(15) -0.24642(11) 0.46877(15) 0.0410(4) Uani 1 1 d . . .
O3 O 1.09579(13) 0.02454(9) 0.16925(13) 0.0286(4) Uani 1 1 d . . .
O4 O 0.96591(13) 0.10140(9) 0.20627(14) 0.0302(4) Uani 1 1 d . . .
O5 O 0.60641(12) 0.05718(9) 0.13528(13) 0.0292(4) Uani 1 1 d . . .
O6 O 0.51074(13) -0.01649(11) 0.22328(16) 0.0403(4) Uani 1 1 d . . .
N1 N 1.04455(15) -0.19929(10) 0.56508(15) 0.0258(4) Uani 1 1 d . . .
C1 C 1.15476(18) -0.24092(12) 0.6223(2) 0.0264(5) Uani 1 1 d . . .
C2 C 1.2261(2) -0.22252(14) 0.7378(2) 0.0341(5) Uani 1 1 d . . .
H2A H 1.2045 -0.1835 0.7800 0.041 Uiso 1 1 calc R . .
C3 C 1.3310(2) -0.26308(15) 0.7904(2) 0.0435(6) Uani 1 1 d . . .
H3A H 1.3796 -0.2518 0.8689 0.052 Uiso 1 1 calc R . .
C4 C 1.3636(2) -0.32000(15) 0.7269(3) 0.0443(7) Uani 1 1 d . . .
H4A H 1.4343 -0.3466 0.7626 0.053 Uiso 1 1 calc R . .
C5 C 1.2919(2) -0.33771(14) 0.6110(3) 0.0410(6) Uani 1 1 d . . .
H5A H 1.3146 -0.3760 0.5684 0.049 Uiso 1 1 calc R . .
C6 C 1.1860(2) -0.29854(13) 0.5575(2) 0.0326(5) Uani 1 1 d . . .
H6A H 1.1367 -0.3107 0.4796 0.039 Uiso 1 1 calc R . .
C7 C 0.94669(19) -0.22171(12) 0.58687(18) 0.0257(5) Uani 1 1 d . . .
C8 C 0.84069(18) -0.18857(12) 0.52315(18) 0.0247(5) Uani 1 1 d . . .
C9 C 0.82746(18) -0.12862(12) 0.43270(17) 0.0229(4) Uani 1 1 d . . .
C10 C 0.93126(17) -0.10294(12) 0.41759(17) 0.0211(4) Uani 1 1 d . . .
C11 C 1.04103(18) -0.13794(12) 0.48605(17) 0.0233(4) Uani 1 1 d . . .
C15 C 0.92704(17) -0.04228(11) 0.33397(17) 0.0200(4) Uani 1 1 d . . .
C17 C 0.71657(17) -0.03480(12) 0.28144(17) 0.0222(4) Uani 1 1 d . . .
C16 C 0.81645(17) -0.00946(12) 0.26587(18) 0.0218(4) Uani 1 1 d . . .
H16A H 0.8108 0.0298 0.2097 0.026 Uiso 1 1 calc R . .
C18 C 0.72137(18) -0.09422(12) 0.36418(18) 0.0243(5) Uani 1 1 d . . .
H18A H 0.6532 -0.1106 0.3732 0.029 Uiso 1 1 calc R . .
C13 C 1.13972(18) -0.05191(12) 0.39181(18) 0.0233(4) Uani 1 1 d . . .
C14 C 1.03322(17) -0.01828(12) 0.31995(18) 0.0224(4) Uani 1 1 d . . .
C12 C 1.14173(18) -0.11091(13) 0.47336(19) 0.0257(5) Uani 1 1 d . . .
H12A H 1.2132 -0.1330 0.5210 0.031 Uiso 1 1 calc R . .
C23 C 1.02653(17) 0.04263(12) 0.22928(18) 0.0228(4) Uani 1 1 d . . .
C20 C 0.7339(2) -0.21372(12) 0.54319(18) 0.0267(5) Uani 1 1 d . . .
C19 C 0.9641(2) -0.28389(14) 0.6812(2) 0.0323(5) Uani 1 1 d . . .
H19A H 0.8907 -0.2948 0.6887 0.048 Uiso 1 1 calc R . .
H19B H 1.0193 -0.2651 0.7564 0.048 Uiso 1 1 calc R . .
H19C H 0.9933 -0.3316 0.6588 0.048 Uiso 1 1 calc R . .
C22 C 1.25641(18) -0.02671(14) 0.3889(2) 0.0307(5) Uani 1 1 d . . .
H22A H 1.2442 0.0139 0.3296 0.046 Uiso 1 1 calc R . .
H22B H 1.2937 -0.0716 0.3692 0.046 Uiso 1 1 calc R . .
H22C H 1.3053 -0.0065 0.4660 0.046 Uiso 1 1 calc R . .
C24 C 1.1036(2) 0.08346(14) 0.0852(2) 0.0317(5) Uani 1 1 d . . .
H24A H 1.1234 0.1349 0.1237 0.038 Uiso 1 1 calc R . .
H24B H 1.0296 0.0879 0.0178 0.038 Uiso 1 1 calc R . .
C25 C 1.1977(2) 0.05585(17) 0.0441(2) 0.0420(6) Uani 1 1 d . . .
H25A H 1.2063 0.0933 -0.0121 0.063 Uiso 1 1 calc R . .
H25B H 1.1770 0.0049 0.0062 0.063 Uiso 1 1 calc R . .
H25C H 1.2703 0.0516 0.1117 0.063 Uiso 1 1 calc R . .
C26 C 0.60121(18) 0.00149(12) 0.21252(19) 0.0252(5) Uani 1 1 d . . .
C27 C 0.49695(19) 0.09563(14) 0.0671(2) 0.0338(5) Uani 1 1 d . . .
H27A H 0.5094 0.1343 0.0146 0.051 Uiso 1 1 calc R . .
H27B H 0.4671 0.1214 0.1207 0.051 Uiso 1 1 calc R . .
H27C H 0.4416 0.0567 0.0206 0.051 Uiso 1 1 calc R . .
C21 C 0.6337(2) -0.21541(16) 0.6776(2) 0.0399(6) Uani 1 1 d . . .
H21A H 0.6553 -0.2189 0.7636 0.048 Uiso 1 1 calc R . .
H21B H 0.6059 -0.2672 0.6436 0.048 Uiso 1 1 calc R . .
C28 C 0.5375(2) -0.15596(18) 0.6273(3) 0.0509(7) Uani 1 1 d . . .
H28A H 0.4713 -0.1718 0.6456 0.076 Uiso 1 1 calc R . .
H28B H 0.5150 -0.1531 0.5420 0.076 Uiso 1 1 calc R . .
H28C H 0.5643 -0.1048 0.6618 0.076 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
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
C20 O1 C21 116.27(17) . .
C23 O3 C24 116.37(16) . .
C26 O5 C27 115.53(16) . .
C7 N1 C11 121.85(17) . .
C7 N1 C1 120.40(17) . .
C11 N1 C1 117.73(17) . .
C2 C1 C6 121.4(2) . .
C2 C1 N1 120.06(19) . .
C6 C1 N1 118.6(2) . .
C1 C2 C3 118.9(2) . .
C4 C3 C2 120.4(2) . .
C5 C4 C3 120.3(2) . .
C4 C5 C6 120.1(2) . .
C5 C6 C1 118.9(2) . .
C8 C7 N1 120.18(19) . .
C8 C7 C19 123.12(19) . .
N1 C7 C19 116.69(19) . .
C7 C8 C9 121.48(19) . .
C7 C8 C20 120.82(19) . .
C9 C8 C20 117.69(18) . .
C18 C9 C10 119.27(18) . .
C18 C9 C8 123.64(19) . .
C10 C9 C8 117.06(18) . .
C11 C10 C15 118.83(18) . .
C11 C10 C9 120.30(18) . .
C15 C10 C9 120.87(18) . .
C12 C11 N1 121.36(18) . .
C12 C11 C10 119.83(18) . .
N1 C11 C10 118.81(18) . .
C16 C15 C10 117.56(18) . .
C16 C15 C14 122.92(18) . .
C10 C15 C14 119.50(18) . .
C16 C17 C18 121.16(19) . .
C16 C17 C26 120.87(18) . .
C18 C17 C26 117.96(18) . .
C17 C16 C15 121.00(18) . .
C9 C18 C17 120.13(18) . .
C12 C13 C14 119.46(19) . .
C12 C13 C22 116.90(18) . .
C14 C13 C22 123.63(19) . .
C13 C14 C15 119.94(19) . .
C13 C14 C23 121.28(18) . .
C15 C14 C23 118.77(18) . .
C11 C12 C13 122.33(19) . .
O4 C23 O3 121.69(19) . .
O4 C23 C14 126.58(18) . .
O3 C23 C14 111.71(17) . .
O2 C20 O1 122.9(2) . .
O2 C20 C8 124.14(19) . .
O1 C20 C8 112.97(18) . .
O3 C24 C25 106.45(18) . .
O6 C26 O5 122.49(19) . .
O6 C26 C17 124.48(19) . .
O5 C26 C17 113.03(17) . .
O1 C21 C28 111.4(2) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
O1 C20 1.339(3) .
O1 C21 1.462(3) .
O2 C20 1.209(3) .
O3 C23 1.346(2) .
O3 C24 1.448(3) .
O4 C23 1.209(3) .
O5 C26 1.341(3) .
O5 C27 1.444(3) .
O6 C26 1.210(3) .
N1 C7 1.381(3) .
N1 C11 1.396(3) .
N1 C1 1.453(3) .
C1 C2 1.373(3) .
C1 C6 1.389(3) .
C2 C3 1.388(3) .
C3 C4 1.378(4) .
C4 C5 1.376(4) .
C5 C6 1.388(3) .
C7 C8 1.362(3) .
C7 C19 1.501(3) .
C8 C9 1.450(3) .
C8 C20 1.487(3) .
C9 C18 1.385(3) .
C9 C10 1.427(3) .
C10 C11 1.422(3) .
C10 C15 1.423(3) .
C11 C12 1.385(3) .
C15 C16 1.414(3) .
C15 C14 1.440(3) .
C17 C16 1.382(3) .
C17 C18 1.399(3) .
C17 C26 1.483(3) .
C13 C12 1.392(3) .
C13 C14 1.393(3) .
C13 C22 1.514(3) .
C14 C23 1.479(3) .
C24 C25 1.498(3) .
C21 C28 1.496(4) .
