#------------------------------------------------------------------------------
#$Date: 2021-09-06 15:34:37 +0300 (Mon, 06 Sep 2021) $
#$Revision: 268954 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/15/81/7158145.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_7158145
loop_
_publ_author_name
'Zhan, Shao-Cong'
'Fang, Ren-Jie'
'Sun, Jing'
'Yan, Chao-Guo'
_publ_section_title
;
 Diastereoselective synthesis of spiro[carbazole-3,5'-pyrimidines] and
 spiro[carbazole-3,1'-cyclohexanes] via four-component reaction.
;
_journal_issue                   28
_journal_name_full               'Organic & biomolecular chemistry'
_journal_page_first              6322
_journal_page_last               6327
_journal_paper_doi               10.1039/d1ob01113h
_journal_volume                  19
_journal_year                    2021
_chemical_formula_moiety         'C33 H26 N4 O7'
_chemical_formula_sum            'C33 H26 N4 O7'
_chemical_formula_weight         590.58
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2014/7
_audit_update_record
;
2021-04-20 deposited with the CCDC.	2021-06-22 downloaded from the CCDC.
;
_cell_angle_alpha                99.2210(18)
_cell_angle_beta                 100.1718(17)
_cell_angle_gamma                96.4144(19)
_cell_formula_units_Z            2
_cell_length_a                   8.9596(5)
_cell_length_b                   9.3710(6)
_cell_length_c                   19.8144(11)
_cell_measurement_reflns_used    8145
_cell_measurement_temperature    273(2)
_cell_measurement_theta_max      26.81
_cell_measurement_theta_min      2.22
_cell_volume                     1599.44(16)
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_diffrn_ambient_temperature      273(2)
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0351
_diffrn_reflns_av_unetI/netI     0.0389
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            22802
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.995
_diffrn_reflns_theta_min         2.125
_exptl_absorpt_coefficient_mu    0.088
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6860
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.226
_exptl_crystal_description       block
_exptl_crystal_F_000             616
_exptl_crystal_size_max          0.260
_exptl_crystal_size_mid          0.220
_exptl_crystal_size_min          0.180
_refine_diff_density_max         0.424
_refine_diff_density_min         -0.347
_refine_diff_density_rms         0.038
_refine_ls_extinction_coef       0.028(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_goodness_of_fit_ref   1.015
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     402
_refine_ls_number_reflns         6250
_refine_ls_number_restraints     15
_refine_ls_restrained_S_all      1.042
_refine_ls_R_factor_all          0.0960
_refine_ls_R_factor_gt           0.0602
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0754P)²+0.6870P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1498
_refine_ls_wR_factor_ref         0.1709
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4106
_reflns_number_total             6250
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d1ob01113h2.cif
_cod_data_source_block           4b
_cod_depositor_comments
'Adding full bibliography for 7158139--7158148.cif.'
_cod_database_code               7158145
_shelx_shelxl_version_number     2014/7
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_shelx_estimated_absorpt_t_min   0.978
_shelx_estimated_absorpt_t_max   0.984
loop_
_space_group_symop_operation_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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.7141(3) 0.4112(2) 0.48976(11) 0.0442(5) Uani 1 1 d . . . . .
C2 C 0.7793(3) 0.4788(3) 0.55727(11) 0.0530(6) Uani 1 1 d . . . . .
H2 H 0.8755 0.5351 0.5678 0.064 Uiso 1 1 calc R U . . .
C3 C 0.6973(3) 0.4601(3) 0.60853(12) 0.0563(6) Uani 1 1 d . . . . .
H3 H 0.7391 0.5043 0.6545 0.068 Uiso 1 1 calc R U . . .
C4 C 0.5540(3) 0.3768(3) 0.59290(11) 0.0547(6) Uani 1 1 d . . . . .
H4 H 0.5002 0.3680 0.6285 0.066 Uiso 1 1 calc R U . . .
C5 C 0.4885(3) 0.3062(2) 0.52537(11) 0.0471(5) Uani 1 1 d . . . . .
H5 H 0.3926 0.2493 0.5153 0.057 Uiso 1 1 calc R U . . .
C6 C 0.5703(2) 0.3229(2) 0.47349(10) 0.0405(5) Uani 1 1 d . . . . .
C7 C 0.5425(2) 0.2698(2) 0.39801(10) 0.0382(5) Uani 1 1 d . . . . .
C8 C 0.6779(2) 0.3408(2) 0.37788(11) 0.0404(5) Uani 1 1 d . . . . .
C9 C 0.6902(2) 0.3218(2) 0.30526(11) 0.0421(5) Uani 1 1 d . . . . .
C10 C 0.8217(3) 0.4077(3) 0.28518(11) 0.0488(6) Uani 1 1 d . . . . .
C11 C 0.8903(4) 0.6205(4) 0.2406(2) 0.0903(9) Uani 1 1 d . U . . .
H11A H 0.9350 0.5600 0.2073 0.108 Uiso 1 1 calc R U . . .
H11B H 0.9719 0.6751 0.2776 0.108 Uiso 1 1 calc R U . . .
C12 C 0.8008(5) 0.7200(6) 0.2063(3) 0.1573(19) Uani 1 1 d . U . . .
H12A H 0.7276 0.6648 0.1668 0.236 Uiso 1 1 calc R U . . .
H12B H 0.8683 0.7892 0.1908 0.236 Uiso 1 1 calc R U . . .
H12C H 0.7480 0.7709 0.2386 0.236 Uiso 1 1 calc R U . . .
C13 C 0.4307(2) 0.1797(2) 0.35199(10) 0.0391(5) Uani 1 1 d . . . . .
C14 C 0.2947(2) 0.0996(2) 0.37022(10) 0.0393(5) Uani 1 1 d . . . . .
C15 C 0.1482(3) 0.1354(3) 0.35285(11) 0.0483(6) Uani 1 1 d . . . . .
H15 H 0.1334 0.2139 0.3303 0.058 Uiso 1 1 calc R U . . .
C16 C 0.0243(3) 0.0554(3) 0.36883(13) 0.0574(6) Uani 1 1 d . . . . .
H16 H -0.0727 0.0817 0.3570 0.069 Uiso 1 1 calc R U . . .
C17 C 0.0407(3) -0.0624(3) 0.40178(13) 0.0571(7) Uani 1 1 d . . . . .
C18 C -0.0954(4) -0.1489(4) 0.41893(17) 0.0881(10) Uani 1 1 d . . . . .
H18A H -0.0742 -0.2460 0.4222 0.132 Uiso 1 1 calc R U . . .
H18B H -0.1837 -0.1535 0.3829 0.132 Uiso 1 1 calc R U . . .
H18C H -0.1148 -0.1022 0.4627 0.132 Uiso 1 1 calc R U . . .
C19 C 0.1874(3) -0.0960(3) 0.41977(14) 0.0645(7) Uani 1 1 d . . . . .
H19 H 0.2020 -0.1741 0.4427 0.077 Uiso 1 1 calc R U . . .
C20 C 0.3126(3) -0.0168(3) 0.40467(13) 0.0545(6) Uani 1 1 d . . . . .
H20 H 0.4097 -0.0418 0.4177 0.065 Uiso 1 1 calc R U . . .
C21 C 0.3053(3) 0.1789(3) 0.23016(12) 0.0552(6) Uani 1 1 d . . . . .
C22 C 0.0547(4) 0.0957(6) 0.1553(2) 0.1262(16) Uani 1 1 d . . . . .
H22A H -0.0194 0.0999 0.1849 0.189 Uiso 1 1 calc R U . . .
H22B H 0.0162 0.0210 0.1148 0.189 Uiso 1 1 calc R U . . .
H22C H 0.0732 0.1884 0.1411 0.189 Uiso 1 1 calc R U . . .
C23 C 0.2148(3) -0.0841(4) 0.19337(14) 0.0743(9) Uani 1 1 d . . . . .
C24 C 0.3607(5) -0.2750(3) 0.22326(17) 0.0984(12) Uani 1 1 d . . . . .
H24A H 0.4631 -0.2858 0.2439 0.148 Uiso 1 1 calc R U . . .
H24B H 0.3375 -0.3231 0.1753 0.148 Uiso 1 1 calc R U . . .
H24C H 0.2897 -0.3180 0.2479 0.148 Uiso 1 1 calc R U . . .
C25 C 0.4689(3) -0.0178(3) 0.26406(12) 0.0541(6) Uani 1 1 d . . . . .
C26 C 0.4474(2) 0.1446(2) 0.27521(11) 0.0433(5) Uani 1 1 d . . . . .
C27 C 0.5845(2) 0.2308(2) 0.25692(11) 0.0448(5) Uani 1 1 d . . . . .
C28 C 0.5949(3) 0.2108(3) 0.18146(12) 0.0545(6) Uani 1 1 d . . . . .
C29 C 0.6551(3) 0.0925(4) 0.15114(14) 0.0719(8) Uani 1 1 d . . . . .
H29 H 0.6849 0.0223 0.1770 0.086 Uiso 1 1 calc R U . . .
C30 C 0.6710(3) 0.0789(5) 0.08184(17) 0.0933(12) Uani 1 1 d . . . . .
H30 H 0.7133 0.0008 0.0613 0.112 Uiso 1 1 calc R U . . .
C31 C 0.6239(4) 0.1814(5) 0.04435(15) 0.0939(13) Uani 1 1 d . . . . .
C32 C 0.5628(4) 0.2968(5) 0.07276(17) 0.1001(12) Uani 1 1 d . . . . .
H32 H 0.5309 0.3650 0.0461 0.120 Uiso 1 1 calc R U . . .
C33 C 0.5482(4) 0.3125(4) 0.14199(14) 0.0807(9) Uani 1 1 d . . . . .
H33 H 0.5069 0.3918 0.1619 0.097 Uiso 1 1 calc R U . . .
N1 N 0.7779(2) 0.4209(2) 0.42933(9) 0.0469(5) Uani 1 1 d . . . . .
N2 N 0.1986(2) 0.0620(3) 0.19366(10) 0.0708(7) Uani 1 1 d . . . . .
N3 N 0.3479(3) -0.1171(2) 0.22734(11) 0.0646(6) Uani 1 1 d . . . . .
N4 N 0.6392(5) 0.1628(7) -0.02975(18) 0.1329(17) Uani 1 1 d . . . . .
O1 O 0.9423(2) 0.3689(2) 0.28218(12) 0.0832(6) Uani 1 1 d . . . . .
O2 O 0.7817(2) 0.5309(2) 0.26897(11) 0.0713(5) Uani 1 1 d . U . . .
O3 O 0.2882(2) 0.3042(3) 0.22824(10) 0.0744(6) Uani 1 1 d . . . . .
O4 O 0.1103(3) -0.1788(3) 0.16215(13) 0.1216(10) Uani 1 1 d . . . . .
O5 O 0.5868(3) -0.0545(2) 0.28982(11) 0.0808(6) Uani 1 1 d . . . . .
O6 O 0.5795(5) 0.2438(6) -0.06439(17) 0.192(2) Uani 1 1 d . . . . .
O7 O 0.7071(4) 0.0670(5) -0.05161(17) 0.174(2) 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
C2 C1 C6 121.6(2) . . ?
C2 C1 N1 126.4(2) . . ?
C6 C1 N1 112.07(18) . . ?
C3 C2 C1 117.8(2) . . ?
C3 C2 H2 121.1 . . ?
C1 C2 H2 121.1 . . ?
C2 C3 C4 121.1(2) . . ?
C2 C3 H3 119.4 . . ?
C4 C3 H3 119.4 . . ?
C3 C4 C5 121.5(2) . . ?
C3 C4 H4 119.3 . . ?
C5 C4 H4 119.3 . . ?
C6 C5 C4 117.9(2) . . ?
C6 C5 H5 121.0 . . ?
C4 C5 H5 121.0 . . ?
C5 C6 C1 120.0(2) . . ?
C5 C6 C7 134.7(2) . . ?
C1 C6 C7 105.24(18) . . ?
C13 C7 C6 134.52(19) . . ?
C13 C7 C8 122.58(18) . . ?
C6 C7 C8 102.90(17) . . ?
N1 C8 C9 125.21(19) . . ?
N1 C8 C7 114.68(18) . . ?
C9 C8 C7 120.09(18) . . ?
C27 C9 C8 120.23(19) . . ?
C27 C9 C10 120.71(19) . . ?
C8 C9 C10 119.05(18) . . ?
O1 C10 O2 124.8(2) . . ?
O1 C10 C9 125.3(2) . . ?
O2 C10 C9 109.9(2) . . ?
O2 C11 C12 105.5(3) . . ?
O2 C11 H11A 110.6 . . ?
C12 C11 H11A 110.6 . . ?
O2 C11 H11B 110.6 . . ?
C12 C11 H11B 110.6 . . ?
H11A C11 H11B 108.8 . . ?
C11 C12 H12A 109.5 . . ?
C11 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
C11 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C7 C13 C14 124.66(18) . . ?
C7 C13 C26 118.84(18) . . ?
C14 C13 C26 116.32(17) . . ?
C20 C14 C15 118.1(2) . . ?
C20 C14 C13 119.56(19) . . ?
C15 C14 C13 122.38(19) . . ?
C16 C15 C14 120.5(2) . . ?
C16 C15 H15 119.7 . . ?
C14 C15 H15 119.7 . . ?
C17 C16 C15 121.7(2) . . ?
C17 C16 H16 119.1 . . ?
C15 C16 H16 119.1 . . ?
C16 C17 C19 117.3(2) . . ?
C16 C17 C18 121.2(3) . . ?
C19 C17 C18 121.5(3) . . ?
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 . . ?
C20 C19 C17 121.8(2) . . ?
C20 C19 H19 119.1 . . ?
C17 C19 H19 119.1 . . ?
C19 C20 C14 120.5(2) . . ?
C19 C20 H20 119.7 . . ?
C14 C20 H20 119.7 . . ?
O3 C21 N2 122.8(2) . . ?
O3 C21 C26 120.0(2) . . ?
N2 C21 C26 117.1(3) . . ?
N2 C22 H22A 109.5 . . ?
N2 C22 H22B 109.5 . . ?
H22A C22 H22B 109.5 . . ?
N2 C22 H22C 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
O4 C23 N3 121.7(4) . . ?
O4 C23 N2 119.4(3) . . ?
N3 C23 N2 118.9(2) . . ?
N3 C24 H24A 109.5 . . ?
N3 C24 H24B 109.5 . . ?
H24A C24 H24B 109.5 . . ?
N3 C24 H24C 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 109.5 . . ?
O5 C25 N3 121.8(3) . . ?
O5 C25 C26 120.4(2) . . ?
N3 C25 C26 117.7(2) . . ?
C21 C26 C27 106.66(18) . . ?
C21 C26 C25 115.0(2) . . ?
C27 C26 C25 107.85(18) . . ?
C21 C26 C13 108.01(17) . . ?
C27 C26 C13 115.68(17) . . ?
C25 C26 C13 103.97(17) . . ?
C9 C27 C28 120.88(19) . . ?
C9 C27 C26 122.13(18) . . ?
C28 C27 C26 116.98(18) . . ?
C33 C28 C29 119.4(3) . . ?
C33 C28 C27 120.2(2) . . ?
C29 C28 C27 120.4(2) . . ?
C28 C29 C30 119.8(3) . . ?
C28 C29 H29 120.1 . . ?
C30 C29 H29 120.1 . . ?
C31 C30 C29 119.3(3) . . ?
C31 C30 H30 120.4 . . ?
C29 C30 H30 120.4 . . ?
C32 C31 C30 121.8(3) . . ?
C32 C31 N4 120.0(5) . . ?
C30 C31 N4 118.2(5) . . ?
C31 C32 C33 119.4(4) . . ?
C31 C32 H32 120.3 . . ?
C33 C32 H32 120.3 . . ?
C28 C33 C32 120.3(3) . . ?
C28 C33 H33 119.9 . . ?
C32 C33 H33 119.9 . . ?
C8 N1 C1 105.08(17) . . ?
C21 N2 C23 124.7(2) . . ?
C21 N2 C22 117.0(3) . . ?
C23 N2 C22 118.2(3) . . ?
C23 N3 C25 125.2(3) . . ?
C23 N3 C24 116.5(3) . . ?
C25 N3 C24 118.3(3) . . ?
O7 N4 O6 124.6(4) . . ?
O7 N4 C31 118.3(6) . . ?
O6 N4 C31 117.1(6) . . ?
C10 O2 C11 117.2(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
C1 C2 1.379(3) . ?
C1 C6 1.406(3) . ?
C1 N1 1.426(3) . ?
C2 C3 1.376(3) . ?
C2 H2 0.9300 . ?
C3 C4 1.383(4) . ?
C3 H3 0.9300 . ?
C4 C5 1.387(3) . ?
C4 H4 0.9300 . ?
C5 C6 1.382(3) . ?
C5 H5 0.9300 . ?
C6 C7 1.466(3) . ?
C7 C13 1.338(3) . ?
C7 C8 1.466(3) . ?
C8 N1 1.299(3) . ?
C8 C9 1.447(3) . ?
C9 C27 1.334(3) . ?
C9 C10 1.500(3) . ?
C10 O1 1.186(3) . ?
C10 O2 1.318(3) . ?
C11 O2 1.459(3) . ?
C11 C12 1.467(5) . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C12 H12A 0.9600 . ?
C12 H12B 0.9600 . ?
C12 H12C 0.9600 . ?
C13 C14 1.489(3) . ?
C13 C26 1.541(3) . ?
C14 C20 1.386(3) . ?
C14 C15 1.390(3) . ?
C15 C16 1.381(3) . ?
C15 H15 0.9300 . ?
C16 C17 1.378(4) . ?
C16 H16 0.9300 . ?
C17 C19 1.385(4) . ?
C17 C18 1.507(3) . ?
C18 H18A 0.9600 . ?
C18 H18B 0.9600 . ?
C18 H18C 0.9600 . ?
C19 C20 1.378(3) . ?
C19 H19 0.9300 . ?
C20 H20 0.9300 . ?
C21 O3 1.206(3) . ?
C21 N2 1.380(3) . ?
C21 C26 1.517(3) . ?
C22 N2 1.471(4) . ?
C22 H22A 0.9600 . ?
C22 H22B 0.9600 . ?
C22 H22C 0.9600 . ?
C23 O4 1.216(3) . ?
C23 N3 1.356(4) . ?
C23 N2 1.392(4) . ?
C24 N3 1.487(4) . ?
C24 H24A 0.9600 . ?
C24 H24B 0.9600 . ?
C24 H24C 0.9600 . ?
C25 O5 1.201(3) . ?
C25 N3 1.360(3) . ?
C25 C26 1.541(3) . ?
C26 C27 1.524(3) . ?
C27 C28 1.498(3) . ?
C28 C33 1.381(4) . ?
C28 C29 1.384(4) . ?
C29 C30 1.392(4) . ?
C29 H29 0.9300 . ?
C30 C31 1.364(6) . ?
C30 H30 0.9300 . ?
C31 C32 1.354(6) . ?
C31 N4 1.483(4) . ?
C32 C33 1.387(4) . ?
C32 H32 0.9300 . ?
C33 H33 0.9300 . ?
N4 O7 1.206(7) . ?
N4 O6 1.209(7) . ?
