#------------------------------------------------------------------------------
#$Date: 2016-02-18 16:37:37 +0100 (jue 18 de feb de 2016) $
#$Revision: 176729 $
#$URL: svn://www.crystallography.net/cod/cif/1/51/58/1515842.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_1515842
loop_
_publ_author_name
'Movassaghi, Mohammad'
'Siegel, Dustin S.'
'Han, Sunkyu'
_publ_section_title
;
 Total synthesis of all (-)-Agelastatin alkaloids.
;
_journal_issue                   5
_journal_name_full
'Chemical science (Royal Society of Chemistry : 2010)'
_journal_page_first              561
_journal_page_last               566
_journal_paper_doi               10.1039/c0sc00351d
_journal_volume                  1
_journal_year                    2010
_chemical_absolute_configuration rmad
_chemical_formula_sum            'C12 H12 Br2 N4 O3'
_chemical_formula_weight         420.08
_chemical_name_systematic
;
?
;
_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
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 100.117(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   6.7838(7)
_cell_length_b                   8.1180(9)
_cell_length_c                   12.9579(14)
_cell_measurement_reflns_used    9891
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      30.58
_cell_measurement_theta_min      2.51
_cell_volume                     702.51(13)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_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  0.0338
_diffrn_reflns_av_sigmaI/netI    0.0435
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            12240
_diffrn_reflns_theta_full        29.13
_diffrn_reflns_theta_max         29.13
_diffrn_reflns_theta_min         1.60
_exptl_absorpt_coefficient_mu    5.785
_exptl_absorpt_correction_T_max  0.5954
_exptl_absorpt_correction_T_min  0.2366
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Sheldrick, 2008)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.986
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             412
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.492
_refine_diff_density_min         -0.270
_refine_diff_density_rms         0.076
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.012(6)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.009
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     200
_refine_ls_number_reflns         3735
_refine_ls_number_restraints     200
_refine_ls_restrained_S_all      0.982
_refine_ls_R_factor_all          0.0243
_refine_ls_R_factor_gt           0.0227
_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)+(0.0108P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0488
_refine_ls_wR_factor_ref         0.0491
_reflns_number_gt                3555
_reflns_number_total             3735
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c0sc00351d.txt
_cod_data_source_block           agb
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to
/usr/data/users/saulius/automatic-downloads/retrospective/RSC/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 2281 2013-09-26 08:29:07Z andrius 
;
_cod_original_sg_symbol_H-M      P2(1)
_cod_database_code               1515842
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_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
Br1 Br 0.02190(3) 1.00311(3) -0.143243(18) 0.01825(6) Uani 1 1 d U
N12 N 0.3774(3) 0.9351(2) 0.13772(15) 0.0120(4) Uani 1 1 d U
O1 O 0.0936(2) 1.1219(2) 0.31624(13) 0.0170(4) Uani 1 1 d U
C13 C 0.3279(3) 0.9108(3) 0.03238(18) 0.0134(4) Uani 1 1 d U
Br2 Br 0.49988(3) 0.80716(3) -0.043886(18) 0.02044(6) Uani 1 1 d U
O2 O 0.4807(2) 0.6491(2) 0.44655(13) 0.0148(4) Uani 1 1 d DU
H2O2 H 0.357(3) 0.650(3) 0.419(2) 0.018 Uiso 1 1 d D
N9 N 0.4149(3) 1.0321(2) 0.34376(15) 0.0145(4) Uani 1 1 d DU
H1N9 H 0.430(4) 1.068(3) 0.4091(15) 0.017 Uiso 1 1 d D
C14 C 0.1454(3) 0.9862(3) -0.00276(17) 0.0146(4) Uani 1 1 d U
O3 O 1.1057(2) 0.5858(2) 0.38018(14) 0.0184(4) Uani 1 1 d U
N3 N 0.9069(3) 0.8190(3) 0.37770(15) 0.0147(4) Uani 1 1 d DU
H1N3 H 1.005(3) 0.888(3) 0.390(2) 0.018 Uiso 1 1 d D
C15 C 0.0788(3) 1.0545(3) 0.08489(19) 0.0153(5) Uani 1 1 d U
H3A H -0.0430 1.1122 0.0848 0.018 Uiso 1 1 calc R
N1 N 0.7672(3) 0.5736(2) 0.38146(16) 0.0122(4) Uani 1 1 d U
C11 C 0.2239(3) 1.0217(3) 0.17065(17) 0.0126(4) Uani 1 1 d U
C10 C 0.2364(3) 1.0642(3) 0.28142(18) 0.0130(4) Uani 1 1 d U
C8 C 0.5955(3) 0.9731(3) 0.30772(18) 0.0119(4) Uani 1 1 d U
H6 H 0.6830 1.0660 0.2927 0.014 Uiso 1 1 calc R
C7 C 0.5382(3) 0.8591(3) 0.21251(17) 0.0100(4) Uani 1 1 d U
H7 H 0.6574 0.8405 0.1783 0.012 Uiso 1 1 calc R
C6 C 0.4762(3) 0.6961(3) 0.25797(17) 0.0118(4) Uani 1 1 d U
H8A H 0.5086 0.6017 0.2156 0.014 Uiso 1 1 calc R
H8B H 0.3306 0.6953 0.2591 0.014 Uiso 1 1 calc R
C5 C 0.5979(3) 0.6866(3) 0.37116(17) 0.0096(4) Uani 1 1 d U
C4 C 0.7047(3) 0.8570(3) 0.39163(18) 0.0113(4) Uani 1 1 d U
H10 H 0.7008 0.8984 0.4639 0.014 Uiso 1 1 calc R
C2 C 0.9426(3) 0.6543(3) 0.38102(18) 0.0137(5) Uani 1 1 d U
C16 C 0.7436(3) 0.3975(3) 0.37007(19) 0.0149(5) Uani 1 1 d U
H12A H 0.6600 0.3725 0.3022 0.022 Uiso 1 1 calc R
H12B H 0.6795 0.3544 0.4266 0.022 Uiso 1 1 calc R
H12C H 0.8753 0.3461 0.3736 0.022 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 0.0033 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'
Br Br -0.2901 2.4595 '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
C13 N12 C11 108.44(18)
C13 N12 C7 128.84(19)
C11 N12 C7 121.58(19)
N12 C13 C14 108.33(19)
N12 C13 Br2 122.12(16)
C14 C13 Br2 129.36(18)
C10 N9 C8 125.5(2)
C13 C14 C15 107.7(2)
C13 C14 Br1 125.06(17)
C15 C14 Br1 127.15(17)
C2 N3 C4 111.91(19)
C11 C15 C14 106.9(2)
C2 N1 C16 124.0(2)
C2 N1 C5 111.90(18)
C16 N1 C5 122.83(19)
C15 C11 N12 108.6(2)
C15 C11 C10 131.0(2)
N12 C11 C10 120.32(19)
O1 C10 N9 122.1(2)
O1 C10 C11 122.4(2)
N9 C10 C11 115.46(19)
N9 C8 C4 107.60(18)
N9 C8 C7 110.16(17)
C4 C8 C7 102.86(17)
N12 C7 C8 109.41(17)
N12 C7 C6 113.27(17)
C8 C7 C6 104.97(18)
C7 C6 C5 105.61(17)
O2 C5 N1 109.58(18)
O2 C5 C6 113.45(16)
N1 C5 C6 113.41(18)
O2 C5 C4 112.21(18)
N1 C5 C4 101.94(16)
C6 C5 C4 105.65(18)
N3 C4 C8 113.20(18)
N3 C4 C5 102.22(17)
C8 C4 C5 105.84(17)
O3 C2 N3 126.5(2)
O3 C2 N1 124.6(2)
N3 C2 N1 108.85(19)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
Br1 C14 1.870(2)
N12 C13 1.362(3)
N12 C11 1.384(3)
N12 C7 1.462(3)
O1 C10 1.231(3)
C13 C14 1.384(3)
C13 Br2 1.857(2)
O2 C5 1.397(3)
N9 C10 1.358(3)
N9 C8 1.466(3)
C14 C15 1.408(3)
O3 C2 1.240(3)
N3 C2 1.358(3)
N3 C4 1.448(3)
C15 C11 1.375(3)
N1 C2 1.359(3)
N1 C16 1.443(3)
N1 C5 1.458(3)
C11 C10 1.464(3)
C8 C4 1.528(3)
C8 C7 1.536(3)
C7 C6 1.537(3)
C6 C5 1.553(3)
C5 C4 1.562(3)
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O2 H2O2 O3 0.850(16) 1.770(18) 2.589(2) 161(3) 1_455
N3 H1N3 O1 0.863(17) 2.25(2) 2.940(3) 137(2) 1_655
