#------------------------------------------------------------------------------
#$Date: 2018-03-15 18:33:54 +0200 (Thu, 15 Mar 2018) $
#$Revision: 206958 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/11/19/7111955.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_7111955
loop_
_publ_author_name
'Qi-Long Peng'
'Shi-Peng Luo'
'Xiao-Er Xia'
'Liang-Xian Liu'
'Pei-Qiang Huang'
_publ_section_title
;
 The four-step total synthesis of (--)-chaetominine
;
_journal_name_full               Chem.Commun.
_journal_page_first              1986
_journal_paper_doi               10.1039/c3cc48833k
_journal_volume                  50
_journal_year                    2014
_chemical_absolute_configuration rm
_chemical_formula_moiety         'C22 H18 N4 O4'
_chemical_formula_sum            'C22 H18 N4 O4'
_chemical_formula_weight         420.42
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           5
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  'C 2y'
_symmetry_space_group_name_H-M   'C 1 2 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 95.562(6)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   27.1139(17)
_cell_length_b                   8.5424(5)
_cell_length_c                   8.8326(6)
_cell_measurement_temperature    173(2)
_cell_volume                     2036.2(2)
_computing_cell_refinement       'Bruker FRAMBO'
_computing_data_collection       'Bruker FRAMBO'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'Bruker SHELXTL'
_computing_structure_solution    'Bruker SHELXTL'
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.908
_diffrn_measurement_device_type  'multiwire proportional'
_diffrn_measurement_method       'φ and ω scan'
_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  0.0608
_diffrn_reflns_av_sigmaI/netI    0.1479
_diffrn_reflns_limit_h_max       40
_diffrn_reflns_limit_h_min       -38
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            13969
_diffrn_reflns_theta_full        26.00
_diffrn_reflns_theta_max         32.83
_diffrn_reflns_theta_min         2.32
_exptl_absorpt_coefficient_mu    0.099
_exptl_absorpt_correction_T_max  0.9862
_exptl_absorpt_correction_T_min  0.9775
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Sheldrick, 1996)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.371
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             880
_exptl_crystal_size_max          0.23
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.14
_refine_diff_density_max         0.209
_refine_diff_density_min         -0.219
_refine_diff_density_rms         0.039
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.0(8)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.767
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     360
_refine_ls_number_reflns         6100
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      0.767
_refine_ls_R_factor_all          0.1265
_refine_ls_R_factor_gt           0.0496
_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)+(0.0198P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0589
_refine_ls_wR_factor_ref         0.0688
_reflns_number_gt                2801
_reflns_number_total             6100
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c3cc48833k.txt
_cod_data_source_block           y
_cod_depositor_comments
;

2018-03-15
Z value and formula fixed to values more according to usual
chemical conventions.                 miguel
;
_cod_original_formula_sum            'C44 H40 N8 O10'
_cod_original_formula_weight         840.84
_cod_original_formula_units_Z            2
_cod_original_sg_symbol_H-M      'C 2'
_cod_database_code               7111955
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y, -z'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -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
O4 O 0.13188(6) -1.13388(16) -0.45007(17) 0.0350(4) Uani 1 1 d
N2 N 0.15446(6) -1.07618(18) -0.06226(18) 0.0277(4) Uani 1 1 d
O2 O 0.11620(5) -0.88075(16) 0.05199(16) 0.0395(4) Uani 1 1 d
N3 N 0.08283(6) -0.74070(18) -0.21695(19) 0.0303(4) Uani 1 1 d
C13 C 0.15108(8) -0.8892(2) -0.3177(2) 0.0256(5) Uani 1 1 d
C12 C 0.10744(7) -0.8913(2) -0.2224(2) 0.0260(5) Uani 1 1 d
C8 C 0.16702(7) -1.0570(2) -0.3462(2) 0.0250(5) Uani 1 1 d
C7 C 0.16978(7) -1.1527(2) -0.1969(2) 0.0282(5) Uani 1 1 d
C4 C 0.21962(8) -1.0678(2) -0.3886(2) 0.0284(5) Uani 1 1 d
C3 C 0.25042(8) -1.1381(2) -0.2732(2) 0.0313(5) Uani 1 1 d
N1 N 0.22265(6) -1.18181(19) -0.1533(2) 0.0324(4) Uani 1 1 d
C14 C 0.03316(8) -0.7292(2) -0.2677(3) 0.0380(6) Uani 1 1 d
C11 C 0.12539(7) -0.9480(2) -0.0634(2) 0.0278(5) Uani 1 1 d
C9 C 0.23430(9) -1.1647(3) -0.0016(3) 0.0421(6) Uani 1 1 d
N4 N 0.09375(7) -0.47147(19) -0.1568(3) 0.0551(6) Uani 1 1 d
O1 O 0.27560(6) -1.1765(2) 0.06461(18) 0.0688(6) Uani 1 1 d
C2 C 0.30086(8) -1.1541(2) -0.2816(3) 0.0365(6) Uani 1 1 d
C5 C 0.23935(9) -1.0108(3) -0.5152(3) 0.0385(6) Uani 1 1 d
C15 C 0.01444(9) -0.5702(2) -0.2702(3) 0.0482(7) Uani 1 1 d
C10 C 0.18800(8) -1.1230(3) 0.0707(3) 0.0357(6) Uani 1 1 d
C1 C 0.31962(10) -1.0945(2) -0.4083(3) 0.0425(6) Uani 1 1 d
C17 C 0.10970(9) -0.6130(3) -0.1609(3) 0.0437(6) Uani 1 1 d
C6 C 0.28992(10) -1.0253(3) -0.5235(3) 0.0472(7) Uani 1 1 d
C16 C 0.04473(9) -0.4490(3) -0.2132(3) 0.0596(8) Uani 1 1 d
C22 C 0.16830(12) -1.2558(3) 0.1625(3) 0.0503(7) Uani 1 1 d
C18 C -0.03388(10) -0.5381(3) -0.3336(4) 0.0679(9) Uani 1 1 d
C21 C 0.02661(12) -0.2945(3) -0.2166(5) 0.0939(14) Uani 1 1 d
C19 C -0.05079(12) -0.3865(4) -0.3437(5) 0.0961(13) Uani 1 1 d
C20 C -0.02082(13) -0.2672(4) -0.2807(6) 0.1139(16) Uani 1 1 d
O5 O -0.09087(7) -0.91891(18) -0.3472(2) 0.0387(4) Uani 1 1 d
O3 O 0.00939(6) -0.84608(16) -0.30916(19) 0.0508(5) Uani 1 1 d
H1 H -0.0983(7) -0.917(2) -0.260(2) 0.031(7) Uiso 1 1 d
H2 H 0.1420(6) -0.8448(18) -0.4215(19) 0.014(4) Uiso 1 1 d
H3 H 0.1777(7) -0.831(2) -0.262(2) 0.027(5) Uiso 1 1 d
H4 H -0.0613(11) -0.889(4) -0.357(4) 0.093(12) Uiso 1 1 d
H5 H 0.3523(8) -1.103(2) -0.407(2) 0.029(6) Uiso 1 1 d
H6 H 0.1375(9) -1.224(3) 0.207(2) 0.052(7) Uiso 1 1 d
H7 H 0.1444(8) -0.627(2) -0.124(2) 0.038(6) Uiso 1 1 d
H8 H 0.3214(7) -1.208(2) -0.201(2) 0.031(6) Uiso 1 1 d
H9 H 0.0833(7) -0.9664(19) -0.2697(18) 0.023(5) Uiso 1 1 d
H10 H 0.1943(11) -1.282(3) 0.252(3) 0.090(10) Uiso 1 1 d
H11 H 0.1533(6) -1.248(2) -0.2096(18) 0.025(5) Uiso 1 1 d
H12 H 0.3026(8) -0.991(3) -0.616(2) 0.049(7) Uiso 1 1 d
H13 H 0.2187(7) -0.963(2) -0.591(2) 0.033(6) Uiso 1 1 d
H14 H 0.1944(7) -1.037(2) 0.132(2) 0.032(6) Uiso 1 1 d
H15 H 0.1598(9) -1.346(3) 0.094(3) 0.073(9) Uiso 1 1 d
H16 H 0.1210(10) -1.080(3) -0.518(3) 0.068(10) Uiso 1 1 d
H17 H -0.0545(8) -0.629(3) -0.379(2) 0.057(7) Uiso 1 1 d
H18 H -0.0288(12) -0.162(4) -0.288(3) 0.115(11) Uiso 1 1 d
H19 H -0.0864(12) -0.376(4) -0.393(4) 0.125(12) Uiso 1 1 d
H20 H 0.0478(11) -0.202(4) -0.164(3) 0.118(12) Uiso 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
C11 N2 C7 124.93(16)
C11 N2 C10 122.90(18)
C7 N2 C10 109.13(16)
C17 N3 C14 121.71(18)
C17 N3 C12 119.03(17)
C14 N3 C12 119.27(17)
C12 C13 C8 109.24(16)
N3 C12 C13 113.19(16)
N3 C12 C11 110.98(17)
C13 C12 C11 108.60(16)
O4 C8 C4 113.70(16)
O4 C8 C13 111.03(16)
C4 C8 C13 112.82(16)
O4 C8 C7 106.28(15)
C4 C8 C7 102.10(15)
C13 C8 C7 110.31(16)
N2 C7 N1 102.17(15)
N2 C7 C8 117.76(16)
N1 C7 C8 106.14(17)
C5 C4 C3 119.7(2)
C5 C4 C8 129.07(18)
C3 C4 C8 111.05(19)
C2 C3 C4 122.0(2)
C2 C3 N1 128.16(19)
C4 C3 N1 109.82(18)
C9 N1 C3 128.68(18)
C9 N1 C7 111.65(19)
C3 N1 C7 109.72(16)
O3 C14 N3 120.48(19)
O3 C14 C15 125.88(19)
N3 C14 C15 113.61(19)
O2 C11 N2 122.95(18)
O2 C11 C12 123.41(18)
N2 C11 C12 113.57(18)
O1 C9 N1 125.6(2)
O1 C9 C10 125.6(2)
N1 C9 C10 108.73(19)
C17 N4 C16 115.6(2)
C1 C2 C3 117.0(2)
C4 C5 C6 118.4(2)
C16 C15 C18 119.8(2)
C16 C15 C14 120.0(2)
C18 C15 C14 120.1(2)
N2 C10 C9 101.67(18)
N2 C10 C22 114.02(19)
C9 C10 C22 113.6(2)
C6 C1 C2 121.9(2)
N4 C17 N3 126.0(2)
C1 C6 C5 120.9(3)
C15 C16 N4 122.8(2)
C15 C16 C21 120.0(2)
N4 C16 C21 117.2(2)
C19 C18 C15 120.2(3)
C20 C21 C16 118.6(3)
C18 C19 C20 119.2(3)
C21 C20 C19 122.0(3)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O4 C8 1.418(2)
N2 C11 1.349(2)
N2 C7 1.453(3)
N2 C10 1.469(2)
O2 C11 1.216(2)
N3 C17 1.377(3)
N3 C14 1.381(2)
N3 C12 1.452(2)
C13 C12 1.517(3)
C13 C8 1.525(3)
C12 C11 1.520(3)
C8 C4 1.512(3)
C8 C7 1.547(3)
C7 N1 1.469(2)
C4 C5 1.375(3)
C4 C3 1.390(3)
C3 C2 1.384(3)
C3 N1 1.408(3)
N1 C9 1.355(3)
C14 O3 1.225(2)
C14 C15 1.450(3)
C9 O1 1.216(2)
C9 C10 1.505(3)
N4 C17 1.286(3)
N4 C16 1.387(3)
C2 C1 1.371(3)
C5 C6 1.386(3)
C15 C16 1.385(3)
C15 C18 1.401(3)
C10 C22 1.521(3)
C1 C6 1.369(3)
C16 C21 1.408(3)
C18 C19 1.373(4)
C21 C20 1.374(4)
C19 C20 1.386(4)
