#------------------------------------------------------------------------------
#$Date: 2019-11-03 12:44:18 +0200 (Sun, 03 Nov 2019) $
#$Revision: 221426 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/12/83/4128303.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_4128303
loop_
_publ_author_name
'Thesmar, Pierre'
'Baudoin, Olivier'
_publ_section_title
;
 Efficient and Divergent Total Synthesis of (-)-Epicoccin G and
 (-)-Rostratin A Enabled by Double C(sp³)-H Activation.
;
_journal_issue                   40
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              15779
_journal_page_last               15783
_journal_paper_doi               10.1021/jacs.9b09359
_journal_volume                  141
_journal_year                    2019
_chemical_absolute_configuration ad
_chemical_compound_source        'Pierre Thesmar'
_chemical_formula_moiety         'C22 H27 N2 O8.50'
_chemical_formula_sum            'C22 H27 N2 O8.5'
_chemical_formula_weight         455.46
_chemical_melting_point          ?
_space_group_IT_number           154
_space_group_name_Hall           'P 32 2"'
_space_group_name_H-M_alt        'P 32 2 1'
_symmetry_cell_setting           trigonal
_symmetry_space_group_name_Hall  'P 32 2"'
_symmetry_space_group_name_H-M   'P 32 2 1'
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     other
_audit_creation_date             2018-06-08
_audit_creation_method           CRYSTALS_ver_14.61_build_6949
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                120
_cell_formula_units_Z            6
_cell_length_a                   9.8830(4)
_cell_length_b                   9.8830(4)
_cell_length_c                   36.809(2)
_cell_measurement_reflns_used    9902
_cell_measurement_temperature    123
_cell_measurement_theta_max      69
_cell_measurement_theta_min      4
_cell_volume                     3113.6(2)
_computing_cell_refinement       'Apex2 (Bruker AXS, 2006)'
_computing_data_collection       'Apex2 (Bruker AXS, 2006)'
_computing_data_reduction        'Apex2 (Bruker AXS, 2006)'
_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    'Superflip (Palatinus & Chapuis, 2007)'
_diffrn_ambient_temperature      123
_diffrn_measured_fraction_theta_full 0.989
_diffrn_measured_fraction_theta_max 0.976
_diffrn_measurement_device       Area
_diffrn_measurement_device_type  'Bruker Kappa Apex2'
_diffrn_measurement_method       'φ & ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.031
_diffrn_reflns_av_unetI/netI     0.039
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       43
_diffrn_reflns_limit_l_min       -33
_diffrn_reflns_number            16837
_diffrn_reflns_theta_full        68.000
_diffrn_reflns_theta_max         69.282
_diffrn_reflns_theta_min         3.602
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.949
_exptl_absorpt_correction_T_max  0.98
_exptl_absorpt_correction_T_min  0.88
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Siemens, 1996)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.457
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             1446
_exptl_crystal_recrystallization_method
; 
Cyclohexane / AcOEt
;
_exptl_crystal_size_max          0.130
_exptl_crystal_size_mid          0.120
_exptl_crystal_size_min          0.020
_refine_diff_density_max         0.64
_refine_diff_density_min         -0.29
_refine_ls_abs_structure_details
; 
 Parsons, Flack & Wagner (2013), 
 1133 Friedel Pairs 
;
_refine_ls_abs_structure_Flack   0.05(6)
_refine_ls_extinction_method     None
_refine_ls_goodness_of_fit_ref   0.9809
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     296
_refine_ls_number_reflns         3358
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.0335
_refine_ls_R_factor_gt           0.0327
_refine_ls_shift/su_max          0.0006589
_refine_ls_shift/su_mean         0.0001010
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
;
 Method= Modified Sheldrick 
 w=1/[σ²(F²) + ( 0.05P)² + 1.58P] 
 ,where P=(max(Fo²,0) + 2Fc²)/3 
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_all         0.0854
_refine_ls_wR_factor_gt          0.0845
_refine_ls_wR_factor_ref         0.0842
_reflns_limit_h_max              4
_reflns_limit_h_min              -11
_reflns_limit_k_max              11
_reflns_limit_k_min              0
_reflns_limit_l_max              43
_reflns_limit_l_min              0
_reflns_number_gt                3293
_reflns_number_total             3391
_reflns_threshold_expression     I>2.0σ(I)
_oxford_diffrn_Wilson_B_factor   0.00
_oxford_diffrn_Wilson_scale      0.00
_oxford_refine_ls_r_factor_ref   0.0333
_oxford_refine_ls_scale          0.13028(6)
_oxford_reflns_number_all        3378
_oxford_structure_analysis_title 'P3221 in P3(2)21'
_cod_data_source_file            ja9b09359_si_003.cif
_cod_data_source_block           THP_1149_123K
_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.

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

Automatic conversion script
Id: cif_fix_values 4973 2017-02-22 13:04:09Z antanas 
;
_cod_original_cell_volume        3113.7(2)
_cod_original_sg_symbol_Hall     'P 32 2'
_cod_original_sg_symbol_H-M      'P 32 2 1 '
_cod_original_formula_sum        'C22 H27 N2 O8.50'
_cod_database_code               4128303
_oxford_refine_reflns_threshold_expression_ref I>-3.0\s(I)
_oxford_hooft_y                  0.04(8)
_oxford_bijvoet_difference       0.05(6)
_oxford_refined_flack_x          0.14(14)
loop_
_symmetry_equiv_pos_as_xyz
x,y,z
y,x,-z
x-y,-y,-z+1/3
-y,x-y,z+2/3
-x+y,-x,z+1/3
-x,-x+y,-z+2/3
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
O1 O 0.66558(15) 0.47757(16) 0.41674(3) 0.0186 1.0000 Uani . .
C2 C 0.7235(2) 0.4127(2) 0.39404(5) 0.0206 1.0000 Uani . .
O3 O 0.64241(17) 0.30004(17) 0.37523(4) 0.0259 1.0000 Uani . .
C4 C 0.8980(3) 0.4970(3) 0.39497(6) 0.0310 1.0000 Uani . .
C5 C 0.4978(2) 0.4122(2) 0.41646(4) 0.0155 1.0000 Uani . .
C6 C 0.4502(2) 0.4929(2) 0.38800(4) 0.0149 1.0000 Uani . .
N7 N 0.46591(18) 0.45593(18) 0.35006(4) 0.0162 1.0000 Uani . .
C8 C 0.5978(2) 0.5383(2) 0.33130(5) 0.0179 1.0000 Uani . .
O9 O 0.71833(16) 0.64404(19) 0.34459(4) 0.0281 1.0000 Uani . .
C10 C 0.5972(2) 0.4921(2) 0.29199(4) 0.0167 1.0000 Uani . .
N11 N 0.44079(18) 0.40095(18) 0.27556(4) 0.0160 1.0000 Uani . .
C12 C 0.3045(2) 0.3413(2) 0.29387(5) 0.0162 1.0000 Uani . .
C13 C 0.3138(2) 0.3384(2) 0.33512(5) 0.0162 1.0000 Uani . .
C14 C 0.2005(2) 0.3784(2) 0.35402(5) 0.0197 1.0000 Uani . .
C15 C 0.2745(2) 0.4326(2) 0.39109(5) 0.0162 1.0000 Uani . .
O16 O 0.23217(16) 0.52435(16) 0.41377(3) 0.0199 1.0000 Uani . .
C17 C 0.1903(2) 0.3663(2) 0.42522(5) 0.0178 1.0000 Uani . .
C18 C 0.2732(2) 0.3519(2) 0.45788(5) 0.0191 1.0000 Uani . .
C19 C 0.4513(2) 0.4378(2) 0.45399(4) 0.0172 1.0000 Uani . .
O20 O 0.17742(15) 0.28615(16) 0.27883(3) 0.0203 1.0000 Uani . .
C21 C 0.4466(2) 0.4286(2) 0.23629(4) 0.0153 1.0000 Uani . .
C22 C 0.6067(2) 0.5724(2) 0.23043(5) 0.0173 1.0000 Uani . .
C23 C 0.6808(2) 0.6350(2) 0.26727(5) 0.0185 1.0000 Uani . .
O24 O 0.61612(18) 0.67943(16) 0.20267(3) 0.0234 1.0000 Uani . .
C25 C 0.6958(2) 0.5906(2) 0.19703(5) 0.0206 1.0000 Uani . .
C26 C 0.6347(2) 0.4674(2) 0.16789(5) 0.0246 1.0000 Uani . .
C27 C 0.4637(2) 0.3424(2) 0.17351(5) 0.0205 1.0000 Uani . .
C28 C 0.4409(2) 0.2965(2) 0.21358(5) 0.0168 1.0000 Uani . .
O29 O 0.30721(15) 0.14648(15) 0.22220(3) 0.0186 1.0000 Uani . .
C30 C 0.1618(2) 0.1154(2) 0.21345(5) 0.0189 1.0000 Uani . .
O31 O 0.13375(17) 0.19986(17) 0.19527(4) 0.0239 1.0000 Uani . .
C32 C 0.0435(2) -0.0369(3) 0.22982(6) 0.0278 1.0000 Uani . .
H41 H 0.9365 0.4293 0.3868 0.0505 1.0000 Uiso R .
H43 H 0.9412 0.5871 0.3801 0.0503 1.0000 Uiso R .
H42 H 0.9315 0.5270 0.4198 0.0497 1.0000 Uiso R .
H51 H 0.4463 0.3004 0.4116 0.0200 1.0000 Uiso R .
H61 H 0.5125 0.6089 0.3913 0.0189 1.0000 Uiso R .
H101 H 0.6536 0.4307 0.2902 0.0221 1.0000 Uiso R .
H131 H 0.2914 0.2295 0.3429 0.0180 1.0000 Uiso R .
H142 H 0.1943 0.4638 0.3413 0.0218 1.0000 Uiso R .
H141 H 0.0962 0.2900 0.3564 0.0223 1.0000 Uiso R .
H171 H 0.0791 0.2855 0.4225 0.0234 1.0000 Uiso R .
H182 H 0.2448 0.3896 0.4796 0.0243 1.0000 Uiso R .
H181 H 0.2400 0.2396 0.4608 0.0243 1.0000 Uiso R .
H191 H 0.4944 0.5486 0.4572 0.0223 1.0000 Uiso R .
H192 H 0.4939 0.3983 0.4720 0.0225 1.0000 Uiso R .
H211 H 0.3610 0.4479 0.2290 0.0190 1.0000 Uiso R .
H231 H 0.6564 0.7141 0.2743 0.0223 1.0000 Uiso R .
H232 H 0.7920 0.6752 0.2665 0.0224 1.0000 Uiso R .
H251 H 0.8111 0.6517 0.1990 0.0278 1.0000 Uiso R .
H261 H 0.6481 0.5174 0.1442 0.0333 1.0000 Uiso R .
H262 H 0.6954 0.4139 0.1690 0.0336 1.0000 Uiso R .
H272 H 0.3947 0.3818 0.1661 0.0273 1.0000 Uiso R .
H271 H 0.4380 0.2470 0.1593 0.0268 1.0000 Uiso R .
H281 H 0.5342 0.2889 0.2212 0.0219 1.0000 Uiso R .
H322 H -0.0495 -0.0793 0.2152 0.0413 1.0000 Uiso R .
H321 H 0.0880 -0.1039 0.2294 0.0410 1.0000 Uiso R .
H323 H 0.0254 -0.0172 0.2541 0.0412 1.0000 Uiso R .
O2 O 1.0000 0.9358(3) 0.3333 0.0900 1.0000 Uani S T
H20 H 0.9114 0.8443 0.3365 0.1036 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 0.0181 0.0091 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 0.0311 0.0180 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 0.0492 0.0322 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_atom_site_label_3
_geom_angle
_geom_angle_publ_flag
C2 . O1 C5 116.67(14) yes
O1 . C2 O3 123.40(18) yes
O1 . C2 C4 111.59(17) yes
O3 . C2 C4 125.00(18) yes
C2 . C4 H41 110.5 no
C2 . C4 H43 111.4 no
H41 . C4 H43 108.9 no
C2 . C4 H42 108.4 no
H41 . C4 H42 108.2 no
H43 . C4 H42 109.5 no
O1 . C5 C6 110.82(14) yes
O1 . C5 C19 107.12(13) yes
C6 . C5 C19 109.87(15) yes
O1 . C5 H51 109.9 no
C6 . C5 H51 110.1 no
C19 . C5 H51 109.0 no
C5 . C6 N7 115.07(15) yes
C5 . C6 C15 109.36(14) yes
N7 . C6 C15 102.33(13) yes
C5 . C6 H61 109.9 no
N7 . C6 H61 108.6 no
C15 . C6 H61 111.3 no
C6 . N7 C8 122.16(15) yes
C6 . N7 C13 110.96(14) yes
C8 . N7 C13 126.13(15) yes
N7 . C8 O9 123.37(16) yes
N7 . C8 C10 117.05(16) yes
O9 . C8 C10 119.54(16) yes
C8 . C10 N11 114.88(14) yes
C8 . C10 C23 111.77(15) yes
N11 . C10 C23 103.72(14) yes
C8 . C10 H101 108.7 no
N11 . C10 H101 109.4 no
C23 . C10 H101 108.1 no
C10 . N11 C12 125.04(14) yes
C10 . N11 C21 111.05(14) yes
C12 . N11 C21 120.73(15) yes
N11 . C12 C13 116.75(15) yes
N11 . C12 O20 123.13(16) yes
C13 . C12 O20 120.07(16) yes
C12 . C13 N7 113.91(14) yes
C12 . C13 C14 112.98(15) yes
N7 . C13 C14 102.55(14) yes
C12 . C13 H131 108.3 no
N7 . C13 H131 108.9 no
C14 . C13 H131 110.1 no
C13 . C14 C15 102.41(14) yes
C13 . C14 H142 111.7 no
C15 . C14 H142 110.3 no
C13 . C14 H141 113.3 no
C15 . C14 H141 110.2 no
H142 . C14 H141 108.8 no
C6 . C15 C14 108.88(14) yes
C6 . C15 O16 115.32(14) yes
C14 . C15 O16 120.29(15) yes
C6 . C15 C17 121.07(15) yes
C14 . C15 C17 123.21(16) yes
O16 . C15 C17 60.46(12) yes
C15 . O16 C17 60.72(11) yes
C15 . C17 O16 58.81(11) yes
C15 . C17 C18 120.89(16) yes
O16 . C17 C18 117.07(15) yes
C15 . C17 H171 115.3 no
O16 . C17 H171 116.1 no
C18 . C17 H171 116.3 no
C17 . C18 C19 113.77(15) yes
C17 . C18 H182 110.1 no
C19 . C18 H182 109.5 no
C17 . C18 H181 107.5 no
C19 . C18 H181 106.0 no
H182 . C18 H181 109.8 no
C18 . C19 C5 110.68(14) yes
C18 . C19 H191 110.5 no
C5 . C19 H191 107.6 no
C18 . C19 H192 108.9 no
C5 . C19 H192 109.1 no
H191 . C19 H192 109.9 no
N11 . C21 C22 103.82(14) yes
N11 . C21 C28 113.50(15) yes
C22 . C21 C28 107.29(15) yes
N11 . C21 H211 110.1 no
C22 . C21 H211 111.7 no
C28 . C21 H211 110.2 no
C21 . C22 C23 108.53(14) yes
C21 . C22 O24 116.18(15) yes
C23 . C22 O24 119.61(16) yes
C21 . C22 C25 120.76(16) yes
C23 . C22 C25 124.07(17) yes
O24 . C22 C25 60.11(12) yes
C10 . C23 C22 103.17(15) yes
C10 . C23 H231 110.6 no
C22 . C23 H231 107.7 no
C10 . C23 H232 112.0 no
C22 . C23 H232 111.2 no
H231 . C23 H232 111.7 no
C22 . O24 C25 60.97(11) yes
C22 . C25 O24 58.92(12) yes
C22 . C25 C26 121.61(17) yes
O24 . C25 C26 118.03(17) yes
C22 . C25 H251 116.7 no
O24 . C25 H251 115.2 no
C26 . C25 H251 114.8 no
C25 . C26 C27 113.05(15) yes
C25 . C26 H261 109.2 no
C27 . C26 H261 110.2 no
C25 . C26 H262 107.5 no
C27 . C26 H262 106.6 no
H261 . C26 H262 110.2 no
C26 . C27 C28 108.09(15) yes
C26 . C27 H272 110.5 no
C28 . C27 H272 111.1 no
C26 . C27 H271 110.5 no
C28 . C27 H271 107.2 no
H272 . C27 H271 109.4 no
C21 . C28 C27 109.75(15) yes
C21 . C28 O29 112.41(15) yes
C27 . C28 O29 116.17(15) yes
C21 . C28 H281 105.6 no
C27 . C28 H281 106.7 no
O29 . C28 H281 105.4 no
C28 . O29 C30 120.27(15) yes
O29 . C30 O31 124.25(18) yes
O29 . C30 C32 109.91(16) yes
O31 . C30 C32 125.85(18) yes
C30 . C32 H322 108.1 no
C30 . C32 H321 106.9 no
H322 . C32 H321 111.0 no
C30 . C32 H323 107.8 no
H322 . C32 H323 112.3 no
H321 . C32 H323 110.7 no
H20 6_765 O2 H20 117.5 no
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
O1 C2 . 1.343(2) yes
O1 C5 . 1.447(2) yes
C2 O3 . 1.212(2) yes
C2 C4 . 1.495(3) yes
C4 H41 . 0.967 no
C4 H43 . 0.945 no
C4 H42 . 0.968 no
C5 C6 . 1.526(2) yes
C5 C19 . 1.517(2) yes
C5 H51 . 0.974 no
C6 N7 . 1.471(2) yes
C6 C15 . 1.533(2) yes
C6 H61 . 1.001 no
N7 C8 . 1.333(2) yes
N7 C13 . 1.472(2) yes
C8 O9 . 1.227(2) yes
C8 C10 . 1.516(2) yes
C10 N11 . 1.475(2) yes
C10 C23 . 1.529(2) yes
C10 H101 . 1.010 no
N11 C12 . 1.350(2) yes
N11 C21 . 1.467(2) yes
C12 C13 . 1.522(2) yes
C12 O20 . 1.223(2) yes
C13 C14 . 1.529(3) yes
C13 H131 . 1.025 no
C14 C15 . 1.514(2) yes
C14 H142 . 0.993 no
C14 H141 . 0.966 no
C15 O16 . 1.440(2) yes
C15 C17 . 1.468(2) yes
O16 C17 . 1.464(2) yes
C17 C18 . 1.501(2) yes
C17 H171 . 0.988 no
C18 C19 . 1.531(3) yes
C18 H182 . 0.980 no
C18 H181 . 0.994 no
C19 H191 . 0.964 no
C19 H192 . 0.966 no
C21 C22 . 1.524(3) yes
C21 C28 . 1.527(2) yes
C21 H211 . 0.993 no
C22 C23 . 1.518(2) yes
C22 O24 . 1.440(2) yes
C22 C25 . 1.470(2) yes
C23 H231 . 0.961 no
C23 H232 . 0.965 no
O24 C25 . 1.457(2) yes
C25 C26 . 1.504(3) yes
C25 H251 . 0.990 no
C26 C27 . 1.529(3) yes
C26 H261 . 0.978 no
C26 H262 . 0.980 no
C27 C28 . 1.526(2) yes
C27 H272 . 0.978 no
C27 H271 . 0.994 no
C28 O29 . 1.444(2) yes
C28 H281 . 1.002 no
O29 C30 . 1.350(2) yes
C30 O31 . 1.205(2) yes
C30 C32 . 1.495(3) yes
C32 H322 . 0.961 no
C32 H321 . 0.961 no
C32 H323 . 0.952 no
O2 H20 6_765 0.898 no
O2 H20 . 0.898 no
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_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
C10 H101 O16 6_655 151 1.01 2.57 3.486(3) yes
C14 H142 O3 6_665 134 0.99 2.56 3.324(3) yes
C17 H171 O20 6_555 156 0.99 2.58 3.511(3) yes
C19 H191 O29 6_665 154 0.96 2.59 3.477(3) yes
C28 H281 O16 6_655 168 1.00 2.57 3.561(3) yes
O2 H20 O9 . 179 0.90 1.97 2.865(3) yes
loop_
_oxford_refln_omitted_index_h
_oxford_refln_omitted_index_k
_oxford_refln_omitted_index_l
_oxford_refln_omitted_flag
0 1 6 x
0 0 9 x
-3 3 1 x
0 3 2 x
0 1 15 x
-1 3 0 x
1 2 0 x
0 1 12 x
-3 3 4 x
-1 2 0 x
1 1 0 x
-2 2 3 x
0 0 12 x
-1 2 6 x
1 1 6 x
0 2 7 x
-1 1 19 x
-5 6 1 x
-1 5 3 x
-6 5 1 x
