#------------------------------------------------------------------------------
#$Date: 2016-03-26 03:11:52 +0200 (Sat, 26 Mar 2016) $
#$Revision: 180172 $
#$URL: svn://www.crystallography.net/cod/cif/7/10/68/7106822.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_7106822
loop_
_publ_author_name
'Andrew F. Kyle'
'Pavol Jakubec'
'Dane M. Cockfield'
'Ed Cleator'
'John Skidmore'
'Darren J. Dixon'
_publ_section_title
;
 Total synthesis of (--)-nakadomarin A
;
_journal_name_full               Chem.Commun.
_journal_page_first              10037
_journal_page_last               10039
_journal_paper_doi               10.1039/c1cc13665h
_journal_volume                  47
_journal_year                    2011
_chemical_absolute_configuration unk
_chemical_formula_moiety         'C16 H20 N2 O7'
_chemical_formula_sum            'C16 H20 N2 O7'
_chemical_formula_weight         352.34
_chemical_melting_point          ?
_space_group_IT_number           4
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             10-10-15
_audit_creation_method           CRYSTALS_ver_12.87
_cell_angle_alpha                90
_cell_angle_beta                 109.6310(13)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   9.5453(3)
_cell_length_b                   6.9928(2)
_cell_length_c                   13.4491(4)
_cell_measurement_reflns_used    1788
_cell_measurement_temperature    150
_cell_measurement_theta_max      27
_cell_measurement_theta_min      5
_cell_volume                     845.53(4)
_computing_cell_refinement       'DENZO/SCALEPACK (Otwinowski & Minor, 1997)'
_computing_data_collection       'COLLECT (Nonius, 2001).'
_computing_data_reduction        'DENZO/SCALEPACK (Otwinowski & Minor, 1997)'
_computing_molecular_graphics    'CAMERON (Watkin et al., 1996)'
_computing_publication_material  'CRYSTALS (Betteridge et al., 2003)'
_computing_structure_refinement  'CRYSTALS (Betteridge et al., 2003)'
_computing_structure_solution    'SIR92 (Altomare et al., 1994)'
_diffrn_ambient_temperature      150
_diffrn_measured_fraction_theta_full 0.988
_diffrn_measured_fraction_theta_max 0.987
_diffrn_measurement_device       'Nonius KappaCCD'
_diffrn_measurement_device_type  Area
_diffrn_measurement_method       ω
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.027
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            5923
_diffrn_reflns_theta_full        26.280
_diffrn_reflns_theta_max         27.093
_diffrn_reflns_theta_min         5.173
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.110
_exptl_absorpt_correction_T_max  0.99
_exptl_absorpt_correction_T_min  0.92
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'DENZO/SCALEPACK (Otwinowski & Minor, 1997)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.384
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             372
_exptl_crystal_size_max          0.340
_exptl_crystal_size_mid          0.080
_exptl_crystal_size_min          0.060
_refine_diff_density_max         0.29
_refine_diff_density_min         -0.29
_refine_ls_extinction_coef       180(20)
_refine_ls_extinction_method     'Larson (1970), Equation 22'
_refine_ls_goodness_of_fit_ref   0.9348
_refine_ls_hydrogen_treatment    none
_refine_ls_matrix_type           full
_refine_ls_number_parameters     227
_refine_ls_number_reflns         1988
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0500
_refine_ls_R_factor_gt           0.0387
_refine_ls_shift/su_max          0.0001134
_refine_ls_shift/su_mean         0.0000556
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
;
Method, part 1, Chebychev polynomial, (Watkin, 1994, Prince, 1982)
[weight] = 1.0/[A₀*T₀(x)+A₁*T₁(x) ... +Aₙ₋₁]*Tₙ₋₁(x)]
where Ai are the Chebychev coefficients listed below and x= Fcalc/Fmax
Method = Robust Weighting (Prince, 1982)
W = [weight] * [1-(deltaF/6*sigmaF)²]²
Ai are:
10.5 14.7 6.96 1.84
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_all         0.0926
_refine_ls_wR_factor_gt          0.0796
_refine_ls_wR_factor_ref         0.0926
_reflns_limit_h_max              11
_reflns_limit_h_min              -12
_reflns_limit_k_max              8
_reflns_limit_k_min              0
_reflns_limit_l_max              17
_reflns_limit_l_min              0
_reflns_number_gt                1676
_reflns_number_total             1988
_reflns_threshold_expression     I>2.0σ(I)
_oxford_diffrn_Wilson_B_factor   2.85
_oxford_diffrn_Wilson_scale      1.64
_oxford_refine_ls_r_factor_ref   0.0500
_oxford_refine_ls_scale          0.794(4)
_oxford_reflns_number_all        1988
_oxford_reflns_threshold_expression_ref I>-3.0\s(I)
_oxford_structure_analysis_title 008DJD10
_cod_data_source_file            c1cc13665h.txt
_cod_data_source_block           11
_cod_depositor_comments
;
The following automatic conversions were performed:

'_chemical_melting_point' value 'not measured' was changed to '?' -
the value is undefined or not given.

Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana 

The following automatic conversions were performed:

'_exptl_crystal_density_meas' value 'not measured' was changed to '?'
- the value is perceived as not measured.

Automatic conversion script
Id: cif_fix_values 3008 2015-01-20 13:52:24Z robertas 
;
_cod_original_sg_symbol_H-M      'P 1 21 1 '
_cod_database_code               7106822
loop_
_symmetry_equiv_pos_as_xyz
x,y,z
-x,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_occupancy
_atom_site_adp_type
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
_oxford_atom_site_special_shape
_atom_site_attached_hydrogens
O1 O 0.3956(2) 0.7171(3) 0.27189(17) 0.0325 1.0000 Uani . . . . . . .
C2 C 0.3964(3) 0.5446(5) 0.2553(2) 0.0254 1.0000 Uani . . . . . . .
N3 N 0.3695(3) 0.4029(4) 0.31362(18) 0.0255 1.0000 Uani . . . . . . .
C4 C 0.3849(3) 0.2100(5) 0.2779(2) 0.0258 1.0000 Uani . . . . . . .
C5 C 0.3950(3) 0.2378(5) 0.1674(2) 0.0285 1.0000 Uani . . . . . . .
C6 C 0.4342(3) 0.4555(5) 0.1625(2) 0.0266 1.0000 Uani . . . . . . .
C7 C 0.6006(3) 0.4849(5) 0.1756(2) 0.0271 1.0000 Uani . . . . . . .
C8 C 0.7051(3) 0.4036(5) 0.2770(2) 0.0282 1.0000 Uani . . . . . . .
C9 C 0.7422(4) 0.4798(6) 0.3818(2) 0.0369 1.0000 Uani . . . . . . .
C10 C 0.8436(4) 0.3625(6) 0.4459(3) 0.0416 1.0000 Uani . . . . . . .
O11 O 0.8743(2) 0.2154(5) 0.3908(2) 0.0482 1.0000 Uani . . . . . . .
C12 C 0.7885(3) 0.2433(5) 0.2867(3) 0.0370 1.0000 Uani . . . . . . .
C13 C 0.6350(3) 0.6978(5) 0.1679(2) 0.0312 1.0000 Uani . . . . . . .
N14 N 0.7884(3) 0.7198(4) 0.1631(2) 0.0336 1.0000 Uani . . . . . . .
O15 O 0.8768(3) 0.8214(4) 0.2283(2) 0.0465 1.0000 Uani . . . . . . .
O16 O 0.8171(3) 0.6349(4) 0.09216(19) 0.0471 1.0000 Uani . . . . . . .
C17 C 0.3323(3) 0.5373(5) 0.0593(2) 0.0293 1.0000 Uani . . . . . . .
O18 O 0.3660(2) 0.5664(4) -0.01808(16) 0.0351 1.0000 Uani . . . . . . .
O19 O 0.1957(2) 0.5636(4) 0.06347(17) 0.0414 1.0000 Uani . . . . . . .
C20 C 0.0856(4) 0.6376(7) -0.0317(3) 0.0472 1.0000 Uani . . . . . . .
C21 C 0.2495(4) 0.1162(5) 0.2923(3) 0.0341 1.0000 Uani . . . . . . .
O22 O 0.2434(2) 0.2059(3) 0.38686(17) 0.0339 1.0000 Uani . . . . . . .
C23 C 0.2772(3) 0.4055(5) 0.3827(2) 0.0272 1.0000 Uani . . . . . . .
C24 C 0.3642(4) 0.4699(6) 0.4936(2) 0.0378 1.0000 Uani . . . . . . .
C25 C 0.1363(3) 0.5210(5) 0.3335(3) 0.0341 1.0000 Uani . . . . . . .
H41 H 0.4789 0.1535 0.3279 0.0322 1.0000 Uiso R . . . . . .
H51 H 0.2966 0.2130 0.1148 0.0354 1.0000 Uiso R . . . . . .
H52 H 0.4713 0.1566 0.1563 0.0361 1.0000 Uiso R . . . . . .
H71 H 0.6229 0.4203 0.1160 0.0338 1.0000 Uiso R . . . . . .
H91 H 0.7021 0.5917 0.4016 0.0444 1.0000 Uiso R . . . . . .
H101 H 0.8891 0.3786 0.5206 0.0516 1.0000 Uiso R . . . . . .
H121 H 0.7898 0.1601 0.2324 0.0452 1.0000 Uiso R . . . . . .
H131 H 0.5649 0.7537 0.1024 0.0398 1.0000 Uiso R . . . . . .
H132 H 0.6337 0.7655 0.2320 0.0394 1.0000 Uiso R . . . . . .
H201 H -0.0050 0.6627 -0.0146 0.0721 1.0000 Uiso R . . . . . .
H202 H 0.0671 0.5407 -0.0883 0.0723 1.0000 Uiso R . . . . . .
H203 H 0.1252 0.7571 -0.0500 0.0727 1.0000 Uiso R . . . . . .
H211 H 0.1585 0.1467 0.2312 0.0400 1.0000 Uiso R . . . . . .
H212 H 0.2628 -0.0255 0.3022 0.0405 1.0000 Uiso R . . . . . .
H241 H 0.2994 0.4563 0.5360 0.0578 1.0000 Uiso R . . . . . .
H242 H 0.4547 0.3944 0.5230 0.0583 1.0000 Uiso R . . . . . .
H243 H 0.3876 0.6058 0.4890 0.0583 1.0000 Uiso R . . . . . .
H253 H 0.0753 0.5033 0.3794 0.0535 1.0000 Uiso R . . . . . .
H252 H 0.0848 0.4697 0.2633 0.0531 1.0000 Uiso R . . . . . .
H251 H 0.1632 0.6551 0.3315 0.0530 1.0000 Uiso R . . . . . .
loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_Cromer_Mann_a1
_atom_type_scat_Cromer_Mann_b1
_atom_type_scat_Cromer_Mann_a2
_atom_type_scat_Cromer_Mann_b2
_atom_type_scat_Cromer_Mann_a3
_atom_type_scat_Cromer_Mann_b3
_atom_type_scat_Cromer_Mann_a4
_atom_type_scat_Cromer_Mann_b4
_atom_type_scat_Cromer_Mann_c
_atom_type_scat_source
C 0.0033 0.0016 2.3100 20.8439 1.0200 10.2075 1.5886 0.5687 0.8650 51.6512
0.2156 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
H 0.0000 0.0000 0.4930 10.5109 0.3229 26.1257 0.1402 3.1424 0.0408 57.7998
0.0030 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
N 0.0061 0.0033 12.2126 0.0057 3.1322 9.8933 2.0125 28.9975 1.1663 0.5826
-11.5290 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
O 0.0106 0.0060 3.0485 13.2771 2.2868 5.7011 1.5463 0.3239 0.8670 32.9089
0.2508 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
loop_
_geom_angle_atom_site_label_1
_geom_angle_site_symmetry_1
_geom_angle_atom_site_label_2
_geom_angle_site_symmetry_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
O1 . C2 . N3 . 127.4(3) yes
O1 . C2 . C6 . 124.1(3) yes
N3 . C2 . C6 . 108.5(3) yes
C2 . N3 . C4 . 115.6(2) yes
C2 . N3 . C23 . 129.0(3) yes
C4 . N3 . C23 . 111.5(2) yes
N3 . C4 . C5 . 104.4(2) yes
N3 . C4 . C21 . 100.0(2) yes
C5 . C4 . C21 . 120.7(2) yes
N3 . C4 . H41 . 108.1 no
C5 . C4 . H41 . 111.5 no
C21 . C4 . H41 . 110.6 no
C4 . C5 . C6 . 104.8(2) yes
C4 . C5 . H51 . 108.6 no
C6 . C5 . H51 . 108.9 no
C4 . C5 . H52 . 111.6 no
C6 . C5 . H52 . 110.9 no
H51 . C5 . H52 . 111.7 no
C2 . C6 . C5 . 103.5(2) yes
C2 . C6 . C7 . 111.4(2) yes
C5 . C6 . C7 . 111.8(2) yes
C2 . C6 . C17 . 109.6(2) yes
C5 . C6 . C17 . 108.3(3) yes
C7 . C6 . C17 . 111.8(2) yes
C6 . C7 . C8 . 113.2(2) yes
C6 . C7 . C13 . 110.8(2) yes
C8 . C7 . C13 . 109.6(3) yes
C6 . C7 . H71 . 109.5 no
C8 . C7 . H71 . 107.5 no
C13 . C7 . H71 . 106.0 no
C7 . C8 . C9 . 128.3(3) yes
C7 . C8 . C12 . 126.1(3) yes
C9 . C8 . C12 . 105.6(3) yes
C8 . C9 . C10 . 106.9(3) yes
C8 . C9 . H91 . 126.3 no
C10 . C9 . H91 . 126.8 no
C9 . C10 . O11 . 110.9(3) yes
C9 . C10 . H101 . 125.3 no
O11 . C10 . H101 . 123.9 no
C10 . O11 . C12 . 106.5(3) yes
O11 . C12 . C8 . 110.1(3) yes
O11 . C12 . H121 . 123.0 no
C8 . C12 . H121 . 126.8 no
C7 . C13 . N14 . 109.7(3) yes
C7 . C13 . H131 . 110.3 no
N14 . C13 . H131 . 107.4 no
C7 . C13 . H132 . 110.0 no
N14 . C13 . H132 . 106.7 no
H131 . C13 . H132 . 112.6 no
C13 . N14 . O15 . 118.7(3) yes
C13 . N14 . O16 . 117.4(3) yes
O15 . N14 . O16 . 124.0(3) yes
C6 . C17 . O18 . 125.4(3) yes
C6 . C17 . O19 . 110.4(2) yes
O18 . C17 . O19 . 124.0(3) yes
C17 . O19 . C20 . 116.1(2) yes
O19 . C20 . H201 . 106.9 no
O19 . C20 . H202 . 108.9 no
H201 . C20 . H202 . 111.0 no
O19 . C20 . H203 . 107.4 no
H201 . C20 . H203 . 110.5 no
H202 . C20 . H203 . 111.9 no
C4 . C21 . O22 . 102.3(2) yes
C4 . C21 . H211 . 110.2 no
O22 . C21 . H211 . 110.6 no
C4 . C21 . H212 . 111.7 no
O22 . C21 . H212 . 110.7 no
H211 . C21 . H212 . 110.9 no
C21 . O22 . C23 . 108.2(2) yes
N3 . C23 . O22 . 101.6(2) yes
N3 . C23 . C24 . 112.2(2) yes
O22 . C23 . C24 . 107.9(3) yes
N3 . C23 . C25 . 111.1(2) yes
O22 . C23 . C25 . 110.8(2) yes
C24 . C23 . C25 . 112.6(3) yes
C23 . C24 . H241 . 107.6 no
C23 . C24 . H242 . 111.0 no
H241 . C24 . H242 . 110.9 no
C23 . C24 . H243 . 106.7 no
H241 . C24 . H243 . 109.4 no
H242 . C24 . H243 . 111.1 no
C23 . C25 . H253 . 106.4 no
C23 . C25 . H252 . 108.1 no
H253 . C25 . H252 . 110.4 no
C23 . C25 . H251 . 108.7 no
H253 . C25 . H251 . 110.6 no
H252 . C25 . H251 . 112.3 no
loop_
_geom_bond_atom_site_label_1
_geom_bond_site_symmetry_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
O1 . C2 . 1.227(4) yes
C2 . N3 . 1.340(4) yes
C2 . C6 . 1.543(4) yes
N3 . C4 . 1.456(4) yes
N3 . C23 . 1.480(3) yes
C4 . C5 . 1.534(4) yes
C4 . C21 . 1.519(4) yes
C4 . H41 . 1.004 no
C5 . C6 . 1.574(5) yes
C5 . H51 . 0.983 no
C5 . H52 . 0.974 no
C6 . C7 . 1.551(4) yes
C6 . C17 . 1.515(4) yes
C7 . C8 . 1.505(4) yes
C7 . C13 . 1.536(5) yes
C7 . H71 . 1.004 no
C8 . C9 . 1.436(4) yes
C8 . C12 . 1.356(5) yes
C9 . C10 . 1.338(5) yes
C9 . H91 . 0.947 no
C10 . O11 . 1.356(5) yes
C10 . H101 . 0.959 no
O11 . C12 . 1.378(4) yes
C12 . H121 . 0.937 no
C13 . N14 . 1.495(4) yes
C13 . H131 . 0.991 no
C13 . H132 . 0.987 no
N14 . O15 . 1.220(4) yes
N14 . O16 . 1.231(3) yes
C17 . O18 . 1.205(3) yes
C17 . O19 . 1.336(3) yes
O19 . C20 . 1.451(4) yes
C20 . H201 . 0.982 no
C20 . H202 . 0.991 no
C20 . H203 . 0.982 no
C21 . O22 . 1.437(4) yes
C21 . H211 . 0.997 no
C21 . H212 . 1.003 no
O22 . C23 . 1.438(4) yes
C23 . C24 . 1.511(4) yes
C23 . C25 . 1.517(4) yes
C24 . H241 . 0.978 no
C24 . H242 . 0.975 no
C24 . H243 . 0.983 no
C25 . H253 . 0.989 no
C25 . H252 . 0.975 no
C25 . H251 . 0.975 no
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_site_symmetry_D
_geom_hbond_atom_site_label_H
_geom_hbond_site_symmetry_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_angle_DHA
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_publ_flag
C12 . H121 . O15 1_545 134 0.94 2.52 3.236(5) yes
C13 . H131 . O18 . 122 0.99 2.42 3.063(5) yes
C20 . H201 . O16 1_455 156 0.98 2.57 3.495(5) yes
C21 . H212 . O1 1_545 143 1.00 2.32 3.173(5) yes
