#------------------------------------------------------------------------------
#$Date: 2015-07-05 12:04:36 +0300 (Sun, 05 Jul 2015) $
#$Revision: 140131 $
#$URL: svn://www.crystallography.net/cod/cif/4/12/38/4123800.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_4123800
loop_
_publ_author_name
'Hong, Allen Y.'
'Vanderwal, Christopher D.'
_publ_section_title
;
 A Synthesis of Alsmaphorazine B Demonstrates the Chemical Feasibility of
 a New Biogenetic Hypothesis.
;
_journal_issue                   23
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              7306
_journal_page_last               7309
_journal_paper_doi               10.1021/jacs.5b04686
_journal_volume                  137
_journal_year                    2015
_chemical_formula_sum            'C20 H20 N2 O5'
_chemical_formula_weight         368.38
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2014/7
_cell_angle_alpha                76.5162(10)
_cell_angle_beta                 74.1344(10)
_cell_angle_gamma                80.8092(11)
_cell_formula_units_Z            2
_cell_length_a                   8.3551(7)
_cell_length_b                   8.8733(8)
_cell_length_c                   12.5301(11)
_cell_measurement_reflns_used    3925
_cell_measurement_temperature    133(2)
_cell_measurement_theta_max      28.73
_cell_measurement_theta_min      2.37
_cell_volume                     864.34(13)
_computing_cell_refinement       'Bruker SAINT 8.34a, 2013'
_computing_data_collection       'Bruker APEX2 2014.11-0, 2014'
_computing_data_reduction        'Bruker SAINT 8.34a, 2013'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_solution    'Bruker SHELXTL 2014/4'
_diffrn_ambient_temperature      133(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.908
_diffrn_measurement_device_type  'Bruker SMART 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  0.0215
_diffrn_reflns_av_unetI/netI     0.0285
_diffrn_reflns_laue_measured_fraction_full 0.998
_diffrn_reflns_laue_measured_fraction_max 0.908
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            10435
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.908
_diffrn_reflns_theta_full        25.500
_diffrn_reflns_theta_max         28.813
_diffrn_reflns_theta_min         1.724
_diffrn_source                   'fine-focus sealed tube'
_exptl_absorpt_coefficient_mu    0.103
_exptl_absorpt_correction_T_max  0.8621
_exptl_absorpt_correction_T_min  0.8101
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Bruker SADABS 2014/5'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.415
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    not_measured
_exptl_crystal_description       prism
_exptl_crystal_F_000             388
_exptl_crystal_size_max          0.397
_exptl_crystal_size_mid          0.226
_exptl_crystal_size_min          0.216
_refine_diff_density_max         0.392
_refine_diff_density_min         -0.280
_refine_diff_density_rms         0.048
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.062
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     313
_refine_ls_number_reflns         4088
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.062
_refine_ls_R_factor_all          0.0502
_refine_ls_R_factor_gt           0.0412
_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)+(0.0490P)²+0.3519P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1004
_refine_ls_wR_factor_ref         0.1064
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3405
_reflns_number_total             4088
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            ja5b04686_si_003.cif
_cod_data_source_block           cdv38
_cod_depositor_comments
;
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 3271 2015-04-21 07:52:19Z andrius 

 Adding full bibliography for 4123799--4123800.cif.
;
_cod_database_code               4123800
_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   0.960
_shelx_estimated_absorpt_t_max   0.978
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
O1 O 0.98162(12) 0.75415(11) 0.51624(8) 0.0163(2) Uani 1 1 d . .
O2 O 0.64027(14) 0.93970(12) 0.62197(9) 0.0254(2) Uani 1 1 d . .
O3 O 0.63236(12) 0.70643(11) 0.58192(8) 0.0192(2) Uani 1 1 d . .
O4 O 0.81836(13) 0.39854(11) 0.86599(8) 0.0197(2) Uani 1 1 d . .
O5 O 0.48709(13) 0.43529(12) 0.76093(10) 0.0269(3) Uani 1 1 d . .
N1 N 1.01609(14) 0.95219(13) 0.64523(9) 0.0156(2) Uani 1 1 d . .
N4 N 0.88235(16) 0.50044(13) 0.91590(10) 0.0207(3) Uani 1 1 d . .
C2 C 0.94578(16) 0.82656(15) 0.69512(11) 0.0141(3) Uani 1 1 d . .
C3 C 1.02639(18) 0.57650(15) 0.82777(12) 0.0178(3) Uani 1 1 d . .
C5 C 0.7409(2) 0.62400(17) 0.93549(12) 0.0219(3) Uani 1 1 d . .
C6 C 0.8244(2) 0.77152(17) 0.91371(12) 0.0219(3) Uani 1 1 d . .
C7 C 0.97742(18) 0.75548(15) 0.81220(11) 0.0165(3) Uani 1 1 d . .
C8 C 1.10260(17) 0.86055(15) 0.81244(11) 0.0168(3) Uani 1 1 d . .
C9 C 1.19064(19) 0.86133(17) 0.89115(13) 0.0214(3) Uani 1 1 d . .
C10 C 1.28632(19) 0.98498(17) 0.87146(13) 0.0215(3) Uani 1 1 d . .
C11 C 1.28918(18) 1.10610(16) 0.77792(12) 0.0197(3) Uani 1 1 d . .
C12 C 1.20075(18) 1.10533(16) 0.69888(12) 0.0180(3) Uani 1 1 d . .
C13 C 1.10875(17) 0.98038(15) 0.71749(11) 0.0154(3) Uani 1 1 d . .
C14 C 1.05181(17) 0.52063(15) 0.71788(12) 0.0164(3) Uani 1 1 d . .
C15 C 0.88808(16) 0.56401(14) 0.67916(11) 0.0139(3) Uani 1 1 d . .
C16 C 0.87589(16) 0.74064(15) 0.62842(11) 0.0139(3) Uani 1 1 d . .
C18 C 0.7251(2) 0.25432(18) 0.71559(15) 0.0274(3) Uani 1 1 d . .
H18A H 0.6434 0.1873 0.7143 0.041 Uiso 1 1 calc R U
H18B H 0.7915 0.1996 0.7692 0.041 Uiso 1 1 calc R U
H18C H 0.7992 0.2799 0.6397 0.041 Uiso 1 1 calc R U
C19 C 0.63541(18) 0.40103(16) 0.75152(11) 0.0177(3) Uani 1 1 d . .
C20 C 0.74112(17) 0.50449(15) 0.78174(11) 0.0161(3) Uani 1 1 d . .
C21 C 0.63694(19) 0.62284(17) 0.85135(12) 0.0200(3) Uani 1 1 d . .
C22 C 0.70193(17) 0.80972(15) 0.61275(11) 0.0164(3) Uani 1 1 d . .
C23 C 0.4667(2) 0.7557(2) 0.56327(16) 0.0277(3) Uani 1 1 d . .
H1 H 0.994(3) 0.854(3) 0.4849(18) 0.042(6) Uiso 1 1 d . .
H3A H 1.126(2) 0.5484(19) 0.8584(14) 0.020(4) Uiso 1 1 d . .
H5A H 0.675(2) 0.598(2) 1.0138(15) 0.025(4) Uiso 1 1 d . .
H6A H 0.865(2) 0.777(2) 0.9802(16) 0.031(5) Uiso 1 1 d . .
H6B H 0.746(2) 0.865(2) 0.8988(14) 0.022(4) Uiso 1 1 d . .
H9A H 1.184(2) 0.781(2) 0.9591(15) 0.025(4) Uiso 1 1 d . .
H10A H 1.352(2) 0.987(2) 0.9253(15) 0.024(4) Uiso 1 1 d . .
H11A H 1.354(2) 1.192(2) 0.7690(14) 0.024(4) Uiso 1 1 d . .
H12A H 1.205(2) 1.188(2) 0.6309(15) 0.026(4) Uiso 1 1 d . .
H14A H 1.0824(19) 0.4114(19) 0.7293(13) 0.015(4) Uiso 1 1 d . .
H14B H 1.145(2) 0.5713(18) 0.6588(14) 0.016(4) Uiso 1 1 d . .
H15A H 0.8964(19) 0.5120(17) 0.6159(13) 0.012(4) Uiso 1 1 d . .
H21A H 0.527(2) 0.583(2) 0.8911(15) 0.026(4) Uiso 1 1 d . .
H21B H 0.616(2) 0.727(2) 0.8071(14) 0.020(4) Uiso 1 1 d . .
H23A H 0.437(3) 0.669(2) 0.5431(17) 0.039(5) Uiso 1 1 d . .
H23B H 0.469(2) 0.845(2) 0.5016(18) 0.040(5) Uiso 1 1 d . .
H23C H 0.392(3) 0.779(2) 0.6307(19) 0.045(6) 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
C22 O3 C23 116.05(11)
N4 O4 C20 104.20(9)
C2 N1 C13 107.12(11)
O4 N4 C5 102.92(10)
O4 N4 C3 108.68(10)
C5 N4 C3 107.41(10)
N1 C2 C16 120.11(11)
N1 C2 C7 114.31(12)
C16 C2 C7 123.96(11)
N4 C3 C14 109.29(11)
N4 C3 C7 106.61(11)
C14 C3 C7 111.43(11)
N4 C5 C6 104.36(12)
N4 C5 C21 105.66(11)
C6 C5 C21 114.59(12)
C5 C6 C7 104.46(11)
C8 C7 C2 99.09(10)
C8 C7 C6 108.11(11)
C2 C7 C6 115.23(12)
C8 C7 C3 119.59(12)
C2 C7 C3 112.03(11)
C6 C7 C3 103.36(11)
C9 C8 C13 120.74(13)
C9 C8 C7 131.59(13)
C13 C8 C7 107.39(12)
C8 C9 C10 117.75(13)
C11 C10 C9 121.31(13)
C12 C11 C10 120.90(13)
C13 C12 C11 117.56(13)
C12 C13 C8 121.69(13)
C12 C13 N1 126.97(12)
C8 C13 N1 111.30(11)
C3 C14 C15 108.13(11)
C14 C15 C16 107.62(10)
C14 C15 C20 108.10(10)
C16 C15 C20 116.75(11)
O1 C16 C2 108.65(10)
O1 C16 C22 105.12(10)
C2 C16 C22 113.86(11)
O1 C16 C15 104.80(10)
C2 C16 C15 109.97(10)
C22 C16 C15 113.81(11)
O5 C19 C18 122.65(13)
O5 C19 C20 120.99(12)
C18 C19 C20 116.30(12)
O4 C20 C21 100.82(11)
O4 C20 C19 103.73(10)
C21 C20 C19 113.68(11)
O4 C20 C15 106.51(10)
C21 C20 C15 117.55(11)
C19 C20 C15 112.50(11)
C20 C21 C5 103.12(12)
O2 C22 O3 125.18(13)
O2 C22 C16 125.14(12)
O3 C22 C16 109.61(11)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O1 C16 1.4307(15)
O2 C22 1.2037(17)
O3 C22 1.3361(16)
O3 C23 1.4485(18)
O4 N4 1.4476(14)
O4 C20 1.4596(16)
O5 C19 1.2077(18)
N1 C2 1.2892(17)
N1 C13 1.4257(17)
N4 C5 1.487(2)
N4 C3 1.5194(18)
C2 C16 1.5254(18)
C2 C7 1.5321(18)
C3 C14 1.5204(19)
C3 C7 1.5553(19)
C5 C6 1.5150(19)
C5 C21 1.541(2)
C6 C7 1.552(2)
C7 C8 1.5092(18)
C8 C9 1.384(2)
C8 C13 1.3938(19)
C9 C10 1.396(2)
C10 C11 1.391(2)
C11 C12 1.390(2)
C12 C13 1.3886(19)
C14 C15 1.5370(19)
C15 C16 1.5462(17)
C15 C20 1.5705(18)
C16 C22 1.5304(19)
C18 C19 1.495(2)
C19 C20 1.5395(18)
C20 C21 1.5301(19)
