#------------------------------------------------------------------------------
#$Date: 2015-07-05 12:04:36 +0300 (Sun, 05 Jul 2015) $
#$Revision: 140131 $
#$URL: svn://www.crystallography.net/cod/cif/4/12/37/4123799.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_4123799
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 O4'
_chemical_formula_weight         352.38
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 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                90
_cell_angle_beta                 103.1258(8)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   6.0850(4)
_cell_length_b                   23.7722(15)
_cell_length_c                   11.9955(7)
_cell_measurement_reflns_used    6995
_cell_measurement_temperature    133(2)
_cell_measurement_theta_max      28.26
_cell_measurement_theta_min      2.44
_cell_volume                     1689.86(18)
_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 0.999
_diffrn_measured_fraction_theta_max 0.998
_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  0.0309
_diffrn_reflns_av_unetI/netI     0.0222
_diffrn_reflns_laue_measured_fraction_full 0.999
_diffrn_reflns_laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       29
_diffrn_reflns_limit_k_min       -29
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            18425
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.500
_diffrn_reflns_theta_max         26.372
_diffrn_reflns_theta_min         1.713
_diffrn_source                   'fine-focus sealed tube'
_exptl_absorpt_coefficient_mu    0.097
_exptl_absorpt_correction_T_max  0.8621
_exptl_absorpt_correction_T_min  0.8278
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Bruker SADABS 2014/5'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.385
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    not_measured
_exptl_crystal_description       irregular
_exptl_crystal_F_000             744
_exptl_crystal_size_max          0.233
_exptl_crystal_size_mid          0.182
_exptl_crystal_size_min          0.175
_refine_diff_density_max         1.347
_refine_diff_density_min         -0.196
_refine_diff_density_rms         0.052
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.029
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     311
_refine_ls_number_reflns         3455
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.029
_refine_ls_R_factor_all          0.0572
_refine_ls_R_factor_gt           0.0476
_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)+(0.0635P)²+1.3419P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1210
_refine_ls_wR_factor_ref         0.1278
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2912
_reflns_number_total             3455
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            ja5b04686_si_002.cif
_cod_data_source_block           cdv37
_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               4123799
_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   0.978
_shelx_estimated_absorpt_t_max   0.983
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'
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 0.3808(2) 0.64478(5) 0.52373(10) 0.0196(3) Uani 1 1 d . .
O2 O 0.7111(3) 0.52774(6) 0.61768(13) 0.0342(4) Uani 1 1 d . .
O3 O 0.9742(2) 0.59788(5) 0.86529(12) 0.0287(3) Uani 1 1 d . .
O4 O 1.1971(2) 0.67436(5) 0.90485(11) 0.0207(3) Uani 1 1 d . .
N1 N 1.0406(2) 0.77228(6) 0.77700(12) 0.0169(3) Uani 1 1 d . .
N4 N 0.4408(2) 0.70145(6) 0.49691(12) 0.0188(3) Uani 1 1 d . .
C2 C 0.8839(3) 0.73283(7) 0.72908(14) 0.0152(3) Uani 1 1 d . .
C3 C 0.4775(3) 0.73689(7) 0.60589(14) 0.0180(4) Uani 1 1 d . .
H3A H 0.3664 0.7685 0.5955 0.022 Uiso 1 1 calc R U
C5 C 0.6665(3) 0.69368(8) 0.46854(15) 0.0211(4) Uani 1 1 d . .
C6 C 0.7943(3) 0.74652(8) 0.51384(15) 0.0217(4) Uani 1 1 d . .
C7 C 0.7216(3) 0.76036(7) 0.62770(14) 0.0162(4) Uani 1 1 d . .
C8 C 0.7654(3) 0.82176(8) 0.65497(15) 0.0195(4) Uani 1 1 d . .
C9 C 0.6525(4) 0.86930(8) 0.60709(18) 0.0304(5) Uani 1 1 d . .
C10 C 0.7395(4) 0.92187(9) 0.6460(2) 0.0368(5) Uani 1 1 d . .
C11 C 0.9403(4) 0.92597(8) 0.72852(18) 0.0306(5) Uani 1 1 d . .
C12 C 1.0580(3) 0.87817(8) 0.77606(16) 0.0222(4) Uani 1 1 d . .
C13 C 0.9645(3) 0.82637(7) 0.73905(15) 0.0179(4) Uani 1 1 d . .
C14 C 0.4481(3) 0.69940(8) 0.70355(15) 0.0187(4) Uani 1 1 d . .
C15 C 0.6262(3) 0.65256(7) 0.71566(15) 0.0171(4) Uani 1 1 d . .
C16 C 0.8559(3) 0.67915(7) 0.76142(14) 0.0164(4) Uani 1 1 d . .
C18 C 0.3246(4) 0.54105(9) 0.6219(2) 0.0334(5) Uani 1 1 d . .
C19 C 0.5540(3) 0.55984(8) 0.61087(16) 0.0234(4) Uani 1 1 d . .
C20 C 0.5885(3) 0.62259(7) 0.59545(15) 0.0186(4) Uani 1 1 d . .
C21 C 0.7596(3) 0.63733(8) 0.52458(16) 0.0213(4) Uani 1 1 d . .
C22 C 1.0254(3) 0.65228(7) 0.85006(14) 0.0174(4) Uani 1 1 d . .
C23 C 1.1398(4) 0.56771(10) 0.9487(2) 0.0381(6) Uani 1 1 d . .
H1 H 1.147(4) 0.7666(9) 0.8373(19) 0.026(6) Uiso 1 1 d . .
H5A H 0.645(3) 0.6923(9) 0.3862(19) 0.021(5) Uiso 1 1 d . .
H6A H 0.741(4) 0.7784(10) 0.457(2) 0.036(6) Uiso 1 1 d . .
H6B H 0.959(4) 0.7421(9) 0.5252(18) 0.024(5) Uiso 1 1 d . .
H9A H 0.515(4) 0.8655(9) 0.550(2) 0.030(6) Uiso 1 1 d . .
H10A H 0.662(4) 0.9559(11) 0.615(2) 0.046(7) Uiso 1 1 d . .
H11A H 0.999(4) 0.9620(10) 0.756(2) 0.035(6) Uiso 1 1 d . .
H12A H 1.190(4) 0.8800(9) 0.8333(19) 0.026(6) Uiso 1 1 d . .
H14A H 0.288(4) 0.6846(9) 0.6878(17) 0.021(5) Uiso 1 1 d . .
H14B H 0.469(3) 0.7217(8) 0.7750(17) 0.014(5) Uiso 1 1 d . .
H15A H 0.600(3) 0.6249(9) 0.7730(18) 0.019(5) Uiso 1 1 d . .
H18A H 0.327(4) 0.5011(12) 0.646(2) 0.048(7) Uiso 1 1 d . .
H18B H 0.220(5) 0.5441(12) 0.548(2) 0.051(8) Uiso 1 1 d . .
H18C H 0.274(4) 0.5671(11) 0.677(2) 0.035(6) Uiso 1 1 d . .
H21A H 0.759(4) 0.6084(9) 0.4643(19) 0.024(5) Uiso 1 1 d . .
H21B H 0.910(4) 0.6420(8) 0.5696(18) 0.020(5) Uiso 1 1 d . .
H23A H 1.085(5) 0.5292(13) 0.940(2) 0.058(8) Uiso 1 1 d . .
H23B H 1.150(4) 0.5838(10) 1.021(2) 0.031(6) Uiso 1 1 d . .
H23C H 1.292(4) 0.5700(11) 0.926(2) 0.040(7) 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
N4 O1 C20 103.83(12)
C22 O3 C23 115.09(15)
C2 N1 C13 110.12(14)
O1 N4 C5 103.02(13)
O1 N4 C3 108.50(12)
C5 N4 C3 107.38(13)
C16 C2 N1 130.26(16)
C16 C2 C7 122.01(15)
N1 C2 C7 107.67(14)
C14 C3 N4 108.50(14)
C14 C3 C7 110.95(14)
N4 C3 C7 106.88(13)
N4 C5 C6 103.82(14)
N4 C5 C21 105.78(14)
C6 C5 C21 117.08(15)
C5 C6 C7 105.34(14)
C8 C7 C2 101.05(13)
C8 C7 C3 120.00(14)
C2 C7 C3 113.62(14)
C8 C7 C6 108.82(14)
C2 C7 C6 110.19(14)
C3 C7 C6 103.11(13)
C9 C8 C13 120.40(17)
C9 C8 C7 131.10(16)
C13 C8 C7 108.37(15)
C8 C9 C10 118.66(18)
C11 C10 C9 120.42(19)
C10 C11 C12 121.38(19)
C13 C12 C11 117.23(17)
C12 C13 C8 121.85(16)
C12 C13 N1 128.84(16)
C8 C13 N1 109.29(15)
C3 C14 C15 107.15(14)
C16 C15 C14 107.69(14)
C16 C15 C20 116.67(14)
C14 C15 C20 106.73(14)
C2 C16 C22 120.63(16)
C2 C16 C15 116.97(15)
C22 C16 C15 121.64(15)
O2 C19 C18 122.86(19)
O2 C19 C20 119.77(18)
C18 C19 C20 117.32(17)
O1 C20 C19 107.53(14)
O1 C20 C21 101.41(14)
C19 C20 C21 115.00(15)
O1 C20 C15 107.61(13)
C19 C20 C15 109.06(14)
C21 C20 C15 115.43(15)
C20 C21 C5 102.24(14)
O4 C22 O3 122.30(16)
O4 C22 C16 125.80(16)
O3 C22 C16 111.89(15)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O1 N4 1.4509(19)
O1 C20 1.457(2)
O2 C19 1.211(2)
O3 C22 1.352(2)
O3 C23 1.440(2)
O4 C22 1.220(2)
N1 C2 1.368(2)
N1 C13 1.407(2)
N4 C5 1.499(2)
N4 C3 1.528(2)
C2 C16 1.356(2)
C2 C7 1.529(2)
C3 C14 1.514(2)
C3 C7 1.553(2)
C5 C6 1.512(3)
C5 C21 1.547(3)
C6 C7 1.563(2)
C7 C8 1.506(2)
C8 C9 1.378(3)
C8 C13 1.394(2)
C9 C10 1.395(3)
C10 C11 1.390(3)
C11 C12 1.394(3)
C12 C13 1.387(3)
C14 C15 1.537(2)
C15 C16 1.519(2)
C15 C20 1.578(2)
C16 C22 1.451(2)
C18 C19 1.500(3)
C19 C20 1.523(3)
C20 C21 1.527(3)
