Aminorifamycins and Sporalactams Produced in Culture by a Micromonospora sp. Isolated from a Northeastern-Pacific Marine Sediment Are Potent Antibiotics.
Williams, David E.; Dalisay, Doralyn S.; Chen, Jessie; Polishchuck, Elena A.; Patrick, Brian O.; Narula, Gagandeep; Ko, Mary; Av-Gay, Yossef; Li, Haoxin; Magarvey, Nathan; Andersen, Raymond J.; Organic letters 19 (2017) 766–769; doi:10.1021/acs.orglett.6b03619

data_1545238
_publ_section_title
;
 Aminorifamycins and Sporalactams Produced in Culture by a Micromonospora
 sp. Isolated from a Northeastern-Pacific Marine Sediment Are Potent
 Antibiotics.
;
_journal_issue                   4
_journal_name_full               'Organic letters'
_journal_page_first              766
_journal_page_last               769
_journal_paper_doi               10.1021/acs.orglett.6b03619
_journal_volume                  19
_journal_year                    2017
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C36 H44 N2 O12, 3(C H4 O), 0.25(H2 O)'
_chemical_formula_sum            'C38.625 H55 N2 O14.875'
_chemical_formula_weight         785.34
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_audit_creation_date             2017-01-24
_audit_creation_method
;
Olex2 1.2
(compiled 2017.01.04 svn.r3372 for OlexSys, GUI svn.r5292)
;
_cell_angle_alpha                90
_cell_angle_beta                 110.590(2)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   16.5150(6)
_cell_length_b                   29.0770(10)
_cell_length_c                   19.3491(7)
_cell_measurement_reflns_used    9564
_cell_measurement_temperature    90(2)
_cell_measurement_theta_max      65.12
_cell_measurement_theta_min      2.87
_cell_volume                     8698.0(5)
_computing_cell_refinement       'SAINT v8.34A (Bruker, 2013)'
_computing_data_reduction        'SAINT v8.34A (Bruker, 2013)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'XT (Sheldrick, 2015)'
_diffrn_ambient_temperature      90(2)
_diffrn_detector                 'Bruker APEX2 area detector'
_diffrn_detector_area_resol_mean 7.9
_diffrn_detector_type            'CCD area detector'
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device       'Bruker D8 Kappa diffractometer'
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_monochromator  'mirror optics'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0363
_diffrn_reflns_av_unetI/netI     0.0545
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       34
_diffrn_reflns_limit_k_min       -34
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            51976
_diffrn_reflns_point_group_measured_fraction_full 0.978
_diffrn_reflns_point_group_measured_fraction_max 0.978
_diffrn_reflns_theta_full        65.208
_diffrn_reflns_theta_max         65.208
_diffrn_reflns_theta_min         2.858
_diffrn_source                   'microfocus sealed X-ray tube'
_diffrn_source_type              'Incoatec I\ms'
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.770
_exptl_absorpt_correction_T_max  0.891
_exptl_absorpt_correction_T_min  0.810
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2014/5 (Bruker,2014/5) was used for absorption correction. wR2(int) was 0.0593 before and 0.0510 after correction. The Ratio of minimum to maximum transmission is 0.9086. The \l/2 correction factor is Not present.'
_exptl_crystal_colour            red
_exptl_crystal_colour_primary    red
_exptl_crystal_density_diffrn    1.199
_exptl_crystal_description       prism
_exptl_crystal_F_000             3358
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.762
_refine_diff_density_min         -0.350
_refine_diff_density_rms         0.075
_refine_ls_abs_structure_details
;
 Flack x determined using 11190 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.07(6)
_refine_ls_extinction_coef       0.00079(10)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2016/6 (Sheldrick 2016)'
_refine_ls_goodness_of_fit_ref   1.029
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     2256
_refine_ls_number_reflns         29105
_refine_ls_number_restraints     3263
_refine_ls_restrained_S_all      0.987
_refine_ls_R_factor_all          0.0685
_refine_ls_R_factor_gt           0.0629
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.1202P)^2^+2.4178P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1698
_refine_ls_wR_factor_ref         0.1762
_reflns_Friedel_coverage         0.922
_reflns_Friedel_fraction_full    0.959
_reflns_Friedel_fraction_max     0.959
_reflns_number_gt                26490
_reflns_number_total             29105
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ol6b03619_si_002.cif
_cod_data_source_block           platon_sq
_cod_depositor_comments
;
The following automatic conversions were performed:

'_diffrn_radiation_probe' value 'X-ray' changed to 'x-ray' according
to
/usr/data/users/saulius/crontab/automatic-downloads/rss-feeds/ACS/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 4268 2015-11-12 08:31:59Z antanas 

 Adding full bibliography for 1545238.cif.

2019-07-29
Z value and formula fixed to values more according to usual
chemical conventions.                 miguel
;
_cod_original_formula_weight         3141.37
_cod_original_formula_moiety
'C34.99 H42.48 N2 O10.99, 3(C36 H44 N2 O12), 10.5(C H4 O), H2 O, 0.51(C2 H3 O2)'
_cod_original_formula_units_Z            2
_cod_original_formula_sum        'C154.50 H220 N8 O59.50'
_cod_database_code               1545238
_shelx_shelxl_version_number     2016/6
_shelx_estimated_absorpt_t_max   0.893
_shelx_estimated_absorpt_t_min   0.831
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All C(H,H,H,H,H) groups, All O(H) groups, All O(H,H)
  groups
2. Restrained distances
 O62-H62A
 0.87 with sigma of 0.01
 O62-H62B
 0.87 with sigma of 0.01
 H62A-H62B
 1.4 with sigma of 0.01
 O50-C50
 1.45 with sigma of 0.01
 C54A-H54G = C54A-H54H = C54A-H54F = C54B-H54C = C54B-H54D = C54B-H54E
 0.98 with sigma of 0.01
 H54C-H54D
 1.6 with sigma of 0.01
 O8C-H8C
 0.84 with sigma of 0.01
 O9C-H9C
 0.84 with sigma of 0.01
 H8C-C21C
 1.9 with sigma of 0.01
 H9C-C23C
 1.9 with sigma of 0.01
 H9C-O11C
 2.1 with sigma of 0.01
 H9C-H54C = H9C-H54D = H9C-H54E
 -2.2 with sigma of 0.01
 H9C-H54F = H9C-H54G = H9C-H54H
 -2.2 with sigma of 0.01
 C59-H59A
 0.98 with sigma of 0.01
 H59A-H59B = H59B-H59C = H59C-H59A
 1.6 with sigma of 0.01
 H59B-H11B
 -2.2 with sigma of 0.01
 H60-H59A
 -2.2 with sigma of 0.01
 H60-H59C
 -2.2 with sigma of 0.01
 H59-H60 = H60-H61
 -2.2 with sigma of 0.01
 H19B-H62B
 -2.2 with sigma of 0.01
 H62A-O7B
 2 with sigma of 0.01
 H58A-H58B = H58B-H58C = H58C-H58A
 1.6 with sigma of 0.01
 C58-H58A
 0.98 with sigma of 0.01
 H57-H58C
 -2.2 with sigma of 0.01
 H54F-H54G \\sim H54G-H54H \\sim H54H-H54F \\sim H54C-H54D \\sim H54D-H54E
\\sim H54E-H54C
 with sigma of 0.01
 O10'-C35' \\sim O10A-C35A
 with sigma of 0.02
 C36'-C35' \\sim C36A-C35A
 with sigma of 0.02
 O11'-C35' \\sim O11A-C35A
 with sigma of 0.02
 O54A-C54A \\sim O54B-C54B
 with sigma of 0.02
 O54B-H54C \\sim O54B-H54D \\sim O54B-H54E \\sim O54A-H54F \\sim O54A-H54G
\\sim O54A-H54H
 with sigma of 0.01
 C58-H58A \\sim C58-H58B \\sim C58-H58C
 with sigma of 0.01
 O58-H58A \\sim O58-H58B \\sim O58-H58C
 with sigma of 0.01
 C59-H59A \\sim C59-H59B \\sim C59-H59C
 with sigma of 0.01
 O59-H59A \\sim O59-H59B \\sim O59-H59C
 with sigma of 0.02
 O61-C61 \\sim O59-C59 \\sim O54B_$1-C54B_$1 \\sim O54A_$1-C54A_$1
 with sigma of 0.01
 C55-O55 \\sim O58-C58
 with sigma of 0.02
3. Uiso/Uaniso restraints and constraints
All non-hydrogen atoms have similar U: within 2A with sigma of 0.04 and sigma
for terminal atoms of 0.08
Uanis(O10') \\sim Ueq, Uanis(O10A) \\sim Ueq: with sigma of 0.01 and sigma for
terminal atoms of 0.02
Uanis(O11') = Uanis(O11A)
Uanis(O10') = Uanis(O10A)
4. Rigid body (RIGU) restrains
 All non-hydrogen atoms
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
5. Others
 Sof(O10')=Sof(C35')=Sof(O11')=Sof(C36')=Sof(H36M)=Sof(H36N)=Sof(H36O)=1-FVAR(1)
 Sof(O10A)=Sof(O11A)=Sof(C35A)=Sof(C36A)=Sof(H36A)=Sof(H36B)=Sof(H36C)=FVAR(1)
 Sof(O59)=Sof(H59)=Sof(C59)=Sof(H59A)=Sof(H59B)=Sof(H59C)=1-FVAR(2)
 Sof(O56)=Sof(H56)=Sof(C56)=Sof(H56A)=Sof(H56B)=Sof(H56C)=FVAR(2)
 Fixed Sof: O50(0.75) H50(0.75) C50(0.75) H50A(0.75) H50B(0.75) H50C(0.75)
 O63(0.5) H63(0.5) C63(0.5) H63A(0.5) H63B(0.5) H63C(0.5) C55(0.5) H55A(0.5)
 H55B(0.5) H55C(0.5) O55(0.5) H55(0.5) O54A(0.375) H54A(0.375) O54B(0.375)
 H54B(0.375) C54B(0.375) H54C(0.375) H54D(0.375) H54E(0.375) C54A(0.375)
 H54F(0.375) H54G(0.375) H54H(0.375)
 Fixed X: H50A(0.45879) H50B(0.40922) H50C(0.51167) H63(0.872)
 Fixed Y: H50A(0.327281) H50B(0.34877) H50C(0.35495) H63(0.776239)
 Fixed Z: H50A(1.0909) H50B(1.14105) H50C(1.16445) H63(0.89163)
6.a Ternary CH refined with riding coordinates:
 C20A(H20A), C21A(H21A), C22A(H22A), C23A(H23A), C24A(H24A), C25A(H25A),
 C26A(H26A), C27A(H27A), C20B(H20B), C21B(H21B), C22B(H22B), C23B(H23B),
 C24B(H24B), C25B(H25B), C26B(H26B), C27B(H27B), C20C(H20C), C21C(H21C),
 C22C(H22C), C23C(H23C), C24C(H24C), C25C(H25C), C26C(H26C), C27C(H27C),
 C20D(H20D), C21D(H21D), C22D(H22D), C23D(H23D), C24D(H24D), C25D(H25D),
 C26D(H26D), C27D(H27D)
6.b Aromatic/amide H refined with riding coordinates:
 C17A(H17A), C18A(H18A), C19A(H19A), C28A(H28A), C29A(H29A), C17B(H17B),
 C18B(H18B), C19B(H19B), C28B(H28B), C29B(H29B), C17C(H17C), C18C(H18C),
 C19C(H19C), C28C(H28C), C29C(H29C), C17D(H17D), C18D(H18D), C19D(H19D),
 C28D(H28D), C29D(H29D)
6.c X=CH2 refined with riding coordinates:
 N2B(H2BA,H2BB)
6.d Idealised Me refined as rotating group:
 C13A(H13A,H13B,H13C), C14A(H14A,H14B,H14C), C30A(H30A,H30B,H30C), C31A(H31A,
 H31B,H31C), C32A(H32A,H32B,H32C), C33A(H33A,H33B,H33C), C34A(H34A,H34B,H34C),
 C36A(H36A,H36B,H36C), C13B(H13D,H13E,H13F), C14B(H14D,H14E,H14F), C30B(H30D,
 H30E,H30F), C31B(H31D,H31E,H31F), C32B(H32D,H32E,H32F), C33B(H33D,H33E,H33F),
 C36B(H36D,H36E,H36F), C34B(H34D,H34E,H34F), C13C(H13G,H13H,H13I), C14C(H14G,
 H14H,H14I), C30C(H30G,H30H,H30I), C31C(H31G,H31H,H31I), C32C(H32G,H32H,H32I),
 C33C(H33G,H33H,H33I), C36C(H36G,H36H,H36I), C34C(H34G,H34H,H34I), C13D(H13J,
 H13K,H13L), C14D(H14J,H14K,H14L), C30D(H30J,H30K,H30L), C31D(H31J,H31K,H31L),
 C32D(H32J,H32K,H32L), C33D(H33J,H33K,H33L), C36D(H36J,H36K,H36L), C34D(H34J,
 H34K,H34L), C53(H53A,H53B,H53C), C60(H60A,H60B,H60C), C57(H57A,H57B,H57C),
 C56(H56A,H56B,H56C), C61(H61A,H61B,H61C), C51(H51A,H51B,H51C), C63(H63A,H63B,
 H63C), C52(H52A,H52B,H52C), C55(H55A,H55B,H55C), C36'(H36M,H36N,H36O)
6.e Idealised tetrahedral OH refined as rotating group:
 O3A(H3A), O8A(H8A), O9A(H9A), O3B(H3B), O7B(H7B), O8B(H8B), O11B(H11B),
 O3C(H3C), O12C(H12C), O9D(H9D), O12D(H12D), O50(H50), O53(H53), O60(H60),
 O57(H57), O56(H56), O58(H58), O61(H61), O59(H59), O51(H51), O52(H52), O55(H55),
  O54A(H54A), O54B(H54B)
;
_platon_squeeze_void_probe_radius 1.20
_shelx_res_checksum              82315
_shelx_hkl_checksum              70372
_shelx_fab_checksum              47741
_olex2_submission_special_instructions 'No special instructions were received'