#------------------------------------------------------------------------------
#$Date: 2016-03-21 17:46:13 +0200 (Mon, 21 Mar 2016) $
#$Revision: 178792 $
#$URL: svn://www.crystallography.net/cod/cif/4/10/46/4104659.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_4104659
loop_
_publ_author_name
'Noah Z. Burns'
'Irina N. Krylova'
'Rami N. Hannoush'
'Phil S. Baran'
_publ_section_title
;
 Scalable Total Synthesis and Biological Evaluation of Haouamine A and Its
 Atropisomer
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              9172
_journal_page_last               9173
_journal_paper_doi               10.1021/ja903745s
_journal_volume                  131
_journal_year                    2009
_chemical_formula_sum            'C35 H33 N O4'
_chemical_formula_weight         531.62
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 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                 108.383(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   10.538(7)
_cell_length_b                   28.664(19)
_cell_length_c                   9.364(6)
_cell_measurement_reflns_used    6286
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      25.86
_cell_measurement_theta_min      2.64
_cell_volume                     2684(3)
_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, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.968
_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  0.0650
_diffrn_reflns_av_sigmaI/netI    0.0558
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       28
_diffrn_reflns_limit_k_min       -35
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            20579
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         26.10
_diffrn_reflns_theta_min         2.16
_exptl_absorpt_coefficient_mu    0.085
_exptl_absorpt_correction_T_max  0.923
_exptl_absorpt_correction_T_min  0.669
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.316
_exptl_crystal_description       block
_exptl_crystal_F_000             1128
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.262
_refine_diff_density_min         -0.243
_refine_diff_density_rms         0.055
_refine_ls_extinction_coef       0.0087(12)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.044
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     366
_refine_ls_number_reflns         5161
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.044
_refine_ls_R_factor_all          0.0604
_refine_ls_R_factor_gt           0.0474
_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)+(0.0680P)²+0.7473P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1235
_refine_ls_wR_factor_ref         0.1348
_reflns_number_gt                4193
_reflns_number_total             5161
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja903745s_si_003.cif
_cod_data_source_block           baran94
_cod_database_code               4104659
loop_
_symmetry_equiv_pos_as_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
O1 O 0.65653(11) -0.03350(4) 1.28860(13) 0.0254(3) Uani 1 1 d .
O2 O 0.74807(12) 0.11175(5) 0.47714(13) 0.0309(3) Uani 1 1 d .
O3 O 0.49408(11) 0.11361(4) 0.77320(12) 0.0227(3) Uani 1 1 d .
H3 H 0.4581 0.0880 0.7815 0.034 Uiso 1 1 calc R
O4 O 1.06544(12) 0.05720(4) 1.11991(13) 0.0279(3) Uani 1 1 d .
N1 N 0.74665(13) 0.20483(5) 1.05051(15) 0.0205(3) Uani 1 1 d .
C1 C 0.79756(18) -0.04080(7) 1.3273(2) 0.0321(4) Uani 1 1 d .
H1A H 0.8245 -0.0388 1.2364 0.048 Uiso 1 1 calc R
H1B H 0.8201 -0.0718 1.3727 0.048 Uiso 1 1 calc R
H1C H 0.8447 -0.0169 1.3993 0.048 Uiso 1 1 calc R
C2 C 0.60613(16) 0.00794(6) 1.21704(17) 0.0209(4) Uani 1 1 d .
C3 C 0.68518(16) 0.04372(6) 1.19373(17) 0.0203(4) Uani 1 1 d .
H3A H 0.7797 0.0403 1.2270 0.024 Uiso 1 1 calc R
C4 C 0.62792(15) 0.08477(6) 1.12193(16) 0.0182(4) Uani 1 1 d .
C5 C 0.72045(15) 0.12216(6) 1.10091(16) 0.0178(4) Uani 1 1 d .
C6 C 0.81145(15) 0.11190(6) 1.03558(17) 0.0191(4) Uani 1 1 d .
H6 H 0.8108 0.0815 0.9952 0.023 Uiso 1 1 calc R
C7 C 0.91647(15) 0.14604(6) 1.02169(18) 0.0199(4) Uani 1 1 d .
C8 C 0.93834(15) 0.14081(6) 0.86933(18) 0.0202(4) Uani 1 1 d .
C9 C 0.83215(16) 0.12651(6) 0.74571(18) 0.0217(4) Uani 1 1 d .
H9 H 0.7495 0.1177 0.7587 0.026 Uiso 1 1 calc R
C10 C 0.84690(16) 0.12506(6) 0.60403(18) 0.0237(4) Uani 1 1 d .
C11 C 0.62545(17) 0.09612(7) 0.4948(2) 0.0308(4) Uani 1 1 d .
H11A H 0.6419 0.0681 0.5578 0.046 Uiso 1 1 calc R
H11B H 0.5617 0.0889 0.3959 0.046 Uiso 1 1 calc R
H11C H 0.5885 0.1207 0.5429 0.046 Uiso 1 1 calc R
C12 C 0.46437(15) 0.14594(6) 0.86524(17) 0.0200(4) Uani 1 1 d .
C13 C 0.48793(15) 0.19222(6) 0.84041(18) 0.0220(4) Uani 1 1 d .
H13 H 0.5134 0.2004 0.7550 0.026 Uiso 1 1 calc R
C14 C 0.47504(16) 0.22692(6) 0.93825(18) 0.0226(4) Uani 1 1 d .
C15 C 0.40915(15) 0.21575(6) 1.04153(18) 0.0225(4) Uani 1 1 d .
H15 H 0.3776 0.2397 1.0917 0.027 Uiso 1 1 calc R
C16 C 0.39006(15) 0.16922(6) 1.07040(18) 0.0220(4) Uani 1 1 d .
H16 H 0.3476 0.1615 1.1430 0.026 Uiso 1 1 calc R
C17 C 0.43252(15) 0.13346(6) 0.99390(17) 0.0201(4) Uani 1 1 d .
C18 C 0.48629(15) 0.08885(6) 1.07054(17) 0.0191(4) Uani 1 1 d .
C19 C 0.40960(16) 0.05241(6) 1.09683(17) 0.0210(4) Uani 1 1 d .
H19 H 0.3149 0.0552 1.0635 0.025 Uiso 1 1 calc R
C20 C 0.46759(16) 0.01217(6) 1.17034(17) 0.0219(4) Uani 1 1 d .
H20 H 0.4136 -0.0122 1.1886 0.026 Uiso 1 1 calc R
C21 C 1.04362(15) 0.13853(6) 1.15529(17) 0.0202(4) Uani 1 1 d .
C22 C 1.11153(16) 0.09678(6) 1.20370(18) 0.0235(4) Uani 1 1 d .
C23 C 1.22186(17) 0.09649(7) 1.33399(19) 0.0287(4) Uani 1 1 d .
H23 H 1.2691 0.0683 1.3678 0.034 Uiso 1 1 calc R
C24 C 1.26277(17) 0.13770(7) 1.41461(19) 0.0309(5) Uani 1 1 d .
H24 H 1.3382 0.1373 1.5030 0.037 Uiso 1 1 calc R
C25 C 1.19550(17) 0.17895(7) 1.36808(19) 0.0295(4) Uani 1 1 d .
H25 H 1.2237 0.2069 1.4237 0.035 Uiso 1 1 calc R
C26 C 1.08513(16) 0.17900(6) 1.23763(19) 0.0242(4) Uani 1 1 d .
C27 C 0.99582(17) 0.21949(7) 1.1740(2) 0.0331(5) Uani 1 1 d .
H27A H 1.0452 0.2440 1.1389 0.040 Uiso 1 1 calc R
H27B H 0.9601 0.2331 1.2507 0.040 Uiso 1 1 calc R
C28 C 0.88080(16) 0.19951(6) 1.04019(18) 0.0223(4) Uani 1 1 d .
H28 H 0.8831 0.2163 0.9475 0.027 Uiso 1 1 calc R
C29 C 0.70807(16) 0.25331(6) 1.06911(19) 0.0233(4) Uani 1 1 d .
H29A H 0.7768 0.2745 1.0539 0.028 Uiso 1 1 calc R
H29B H 0.7072 0.2575 1.1737 0.028 Uiso 1 1 calc R
C30 C 0.56804(17) 0.26780(6) 0.95856(19) 0.0246(4) Uani 1 1 d .
H30A H 0.5322 0.2946 1.0003 0.030 Uiso 1 1 calc R
H30B H 0.5767 0.2772 0.8603 0.030 Uiso 1 1 calc R
C31 C 0.71902(16) 0.17181(6) 1.15619(18) 0.0208(4) Uani 1 1 d .
H31A H 0.6305 0.1787 1.1670 0.025 Uiso 1 1 calc R
H31B H 0.7873 0.1753 1.2562 0.025 Uiso 1 1 calc R
C32 C 1.10191(18) 0.01312(7) 1.1936(2) 0.0332(5) Uani 1 1 d .
H32A H 1.1977 0.0077 1.2129 0.050 Uiso 1 1 calc R
H32B H 1.0506 -0.0118 1.1290 0.050 Uiso 1 1 calc R
H32C H 1.0823 0.0133 1.2892 0.050 Uiso 1 1 calc R
C33 C 0.96759(17) 0.13814(6) 0.58375(19) 0.0248(4) Uani 1 1 d .
H33 H 0.9778 0.1372 0.4866 0.030 Uiso 1 1 calc R
C34 C 1.07185(17) 0.15244(6) 0.70671(19) 0.0254(4) Uani 1 1 d .
H34 H 1.1541 0.1615 0.6935 0.030 Uiso 1 1 calc R
C35 C 1.05858(16) 0.15380(6) 0.84896(19) 0.0239(4) Uani 1 1 d .
H35 H 1.1315 0.1636 0.9326 0.029 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'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
C2 O1 C1 117.24(13)
C10 O2 C11 117.23(13)
C22 O4 C32 117.34(14)
C28 N1 C31 112.44(13)
C28 N1 C29 114.62(13)
C31 N1 C29 114.14(14)
C3 C2 O1 123.71(15)
C3 C2 C20 120.74(16)
O1 C2 C20 115.54(15)
C2 C3 C4 120.78(15)
C3 C4 C18 118.76(15)
C3 C4 C5 117.70(14)
C18 C4 C5 123.53(15)
C6 C5 C4 119.79(15)
C6 C5 C31 116.95(15)
C4 C5 C31 123.23(14)
C5 C6 C7 123.53(16)
C6 C7 C8 110.35(13)
C6 C7 C21 108.28(13)
C8 C7 C21 113.54(14)
C6 C7 C28 114.01(14)
C8 C7 C28 107.81(13)
C21 C7 C28 102.76(13)
C35 C8 C9 119.51(16)
C35 C8 C7 121.06(14)
C9 C8 C7 119.21(15)
C10 C9 C8 120.09(16)
O2 C10 C9 123.88(16)
O2 C10 C33 115.77(15)
C9 C10 C33 120.34(15)
O3 C12 C13 117.08(15)
O3 C12 C17 122.39(16)
C13 C12 C17 119.74(15)
C12 C13 C14 121.09(16)
C13 C14 C15 117.86(17)
C13 C14 C30 116.57(16)
C15 C14 C30 122.66(16)
C16 C15 C14 119.36(16)
C15 C16 C17 120.91(16)
C12 C17 C16 117.13(16)
C12 C17 C18 118.56(15)
C16 C17 C18 121.07(15)
C19 C18 C4 119.05(15)
C19 C18 C17 125.25(15)
C4 C18 C17 115.69(14)
C20 C19 C18 121.66(16)
C19 C20 C2 118.96(16)
C26 C21 C22 119.87(15)
C26 C21 C7 112.21(15)
C22 C21 C7 127.78(15)
O4 C22 C21 117.96(14)
O4 C22 C23 122.68(16)
C21 C22 C23 119.36(17)
C22 C23 C24 119.89(18)
C25 C24 C23 121.03(16)
C24 C25 C26 118.80(17)
C21 C26 C25 121.04(17)
C21 C26 C27 112.32(15)
C25 C26 C27 126.58(17)
C26 C27 C28 105.58(15)
N1 C28 C27 115.81(15)
N1 C28 C7 111.95(13)
C27 C28 C7 106.89(13)
N1 C29 C30 114.15(13)
C14 C30 C29 108.53(14)
N1 C31 C5 110.53(14)
C34 C33 C10 119.11(16)
C33 C34 C35 121.09(16)
C34 C35 C8 119.86(15)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O1 C2 1.385(2)
O1 C1 1.430(2)
O2 C10 1.364(2)
O2 C11 1.426(2)
O3 C12 1.368(2)
O4 C22 1.378(2)
O4 C32 1.433(2)
N1 C28 1.455(2)
N1 C31 1.463(2)
N1 C29 1.474(2)
C2 C3 1.381(2)
C2 C20 1.391(2)
C3 C4 1.395(2)
C4 C18 1.421(2)
C4 C5 1.503(2)
C5 C6 1.323(2)
C5 C31 1.516(3)
C6 C7 1.513(2)
C7 C8 1.523(2)
C7 C21 1.533(2)
C7 C28 1.600(3)
C8 C35 1.390(2)
C8 C9 1.394(2)
C9 C10 1.384(2)
C10 C33 1.395(3)
C12 C13 1.383(3)
C12 C17 1.395(2)
C13 C14 1.388(3)
C14 C15 1.394(3)
C14 C30 1.501(3)
C15 C16 1.388(3)
C16 C17 1.402(3)
C17 C18 1.488(2)
C18 C19 1.389(2)
C19 C20 1.383(2)
C21 C26 1.385(2)
C21 C22 1.395(3)
C22 C23 1.395(2)
C23 C24 1.395(3)
C24 C25 1.377(3)
C25 C26 1.396(2)
C26 C27 1.495(3)
C27 C28 1.552(2)
C29 C30 1.568(2)
C33 C34 1.379(2)
C34 C35 1.383(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
O3 H3 O1 0.84 1.96 2.747(2) 156.1 3_657
