Singly and Doubly Neo-Confused Smaragdyrins.
Rao, Yutao; Zhou, Wenjing; Xu, Ling; Zhou, Mingbo; Yin, Bangshao; Tanaka, Takayuki; Osuka, Atsuhiro; Song, Jianxin; Journal of the American Chemical Society 141 (2019) 18836–18844; doi:10.1021/jacs.9b10270

data_4129104
_publ_section_title
;
 Singly and Doubly Neo-Confused Smaragdyrins.
;
_journal_issue                   47
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              18836
_journal_page_last               18844
_journal_paper_doi               10.1021/jacs.9b10270
_journal_volume                  141
_journal_year                    2019
_chemical_formula_moiety         '4(C H Cl3), 2(C50 H45 N5 O2)'
_chemical_formula_sum            'C104 H94 Cl12 N10 O4'
_chemical_formula_weight         1973.29
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             2019-04-07
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_cell_angle_alpha                113.521(3)
_cell_angle_beta                 91.756(2)
_cell_angle_gamma                98.502(2)
_cell_formula_units_Z            2
_cell_length_a                   15.9672(4)
_cell_length_b                   17.4963(5)
_cell_length_c                   19.2176(7)
_cell_measurement_reflns_used    20045
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      71.8010
_cell_measurement_theta_min      4.2850
_cell_volume                     4844.7(3)
_computing_cell_refinement       'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 8.0697
_diffrn_detector_type            EosS2
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  t~exp~   \w     \q     \k     \f   Frames
--------------------------------------------------------------------------
  1  \w    -34.00  43.00   1.00    2.00    --   34.73 -44.00 112.00   77
  2  \w      7.00  74.00   1.00    2.00    --   34.73 -99.00  90.00   67
  3  \w     27.00  73.00   1.00    2.00    --   34.73 -99.00 -30.00   46
  4  \w     37.00  88.00   1.00    2.00    --   34.73-125.00-120.00   51
  5  \w     43.00 131.00   1.00    8.00    --  105.88 -77.00-150.00   88
  6  \w     67.00  93.00   1.00    8.00    --  105.88 -94.00 -60.00   26
  7  \w     54.00 116.00   1.00    8.00    --  105.88-111.00  30.00   62
  8  \w     37.00  62.00   1.00    8.00    --  105.88 -94.00 -60.00   25
  9  \w     49.00 116.00   1.00    8.00    --  105.88-111.00-150.00   67
 10  \w     39.00 133.00   1.00    8.00    --  105.88 -77.00  30.00   94
 11  \w     84.00 112.00   1.00    8.00    --  105.88  30.00 150.00   28
 12  \w     84.00 154.00   1.00    8.00    --  105.88  30.00 120.00   70
 13  \w    130.00 156.00   1.00    8.00    --  105.88  77.00  60.00   26
 14  \w    124.00 166.00   1.00    8.00    --  105.88  77.00   0.00   42
 15  \w    123.00 172.00   1.00    8.00    --  105.88  77.00 -30.00   49
 16  \w    123.00 172.00   1.00    8.00    --  105.88  77.00-120.00   49
 17  \w    123.00 169.00   1.00    8.00    --  105.88  77.00 -60.00   46
 18  \w    123.00 173.00   1.00    8.00    --  105.88  77.00 -90.00   50
 19  \w    117.00 168.00   1.00    8.00    --  105.88  77.00-180.00   51
 20  \w    114.00 173.00   1.00    8.00    --  105.88  77.00-150.00   59
 21  \w     88.00 114.00   1.00    8.00    --  105.88  61.00-150.00   26
 22  \w     88.00 121.00   1.00    8.00    --  105.88  61.00-120.00   33
 23  \w     88.00 114.00   1.00    8.00    --  105.88  61.00-180.00   26
 24  \w     79.00 110.00   1.00    8.00    --  105.88  77.00-180.00   31
 25  \w     79.00 105.00   1.00    8.00    --  105.88  77.00-120.00   26
 26  \w     88.00 114.00   1.00    8.00    --  105.88  61.00 -90.00   26
 27  \w     88.00 114.00   1.00    8.00    --  105.88  61.00 -60.00   26
 28  \w     88.00 113.00   1.00    8.00    --  105.88  61.00 -30.00   25
 29  \w     88.00 114.00   1.00    8.00    --  105.88  61.00   0.00   26
 30  \w    114.00 170.00   1.00    8.00    --  105.88  77.00  30.00   56
 31  \w    122.00 169.00   1.00    8.00    --  105.88  77.00 150.00   47
 32  \w    118.00 152.00   1.00    8.00    --  105.88  61.00  90.00   34
 33  \w    142.00 171.00   1.00    8.00    --  105.88  77.00  90.00   29
 34  \w    112.00 172.00   1.00    8.00    --  105.88  77.00 120.00   60
 35  \w     88.00 121.00   1.00    8.00    --  105.88  61.00  60.00   33
 36  \w     88.00 113.00   1.00    8.00    --  105.88  61.00 120.00   25
 37  \w     88.00 114.00   1.00    8.00    --  105.88  61.00  90.00   26
 38  \w     79.00 105.00   1.00    8.00    --  105.88  77.00  90.00   26
 39  \w     79.00 104.00   1.00    8.00    --  105.88  77.00  60.00   25
 40  \w     88.00 114.00   1.00    8.00    --  105.88  61.00  30.00   26
 41  \w     79.00 104.00   1.00    8.00    --  105.88  77.00 -30.00   25
 42  \w     79.00 105.00   1.00    8.00    --  105.88  77.00 -60.00   26
 43  \w     79.00 105.00   1.00    8.00    --  105.88  77.00 -90.00   26
 44  \w     84.00 130.00   1.00    8.00    --  105.88  30.00 -60.00   46
 45  \w     85.00 117.00   1.00    8.00    --  105.88  30.00  30.00   32
 46  \w     84.00 118.00   1.00    8.00    --  105.88  30.00  60.00   34
 47  \w     84.00 111.00   1.00    8.00    --  105.88  30.00   0.00   27
 48  \w     84.00 112.00   1.00    8.00    --  105.88  30.00 -30.00   28
 49  \w     79.00 104.00   1.00    8.00    --  105.88  77.00  30.00   25
 50  \w     79.00 104.00   1.00    8.00    --  105.88  77.00   0.00   25
 51  \w     84.00 112.00   1.00    8.00    --  105.88  30.00-120.00   28
 52  \w     85.00 110.00   1.00    8.00    --  105.88  30.00-150.00   25
 53  \w     84.00 110.00   1.00    8.00    --  105.88  30.00-180.00   26
 54  \w     79.00 105.00   1.00    8.00    --  105.88  77.00-150.00   26
 55  \w     51.00  98.00   1.00    2.00    --   34.73  57.00-180.00   47
 56  \w     56.00  91.00   1.00    2.00    --   34.73  77.00-120.00   35
 57  \w     68.00  93.00   1.00    2.00    --   34.73  77.00 -60.00   25
 58  \w     59.00 100.00   1.00    2.00    --   34.73  77.00  30.00   41
 59  \w     67.00 104.00   1.00    2.00    --   34.73  38.00  90.00   37
 60  \w     79.00 104.00   1.00    8.00    --  105.88  77.00 150.00   25
 61  \w     88.00 114.00   1.00    8.00    --  105.88  61.00 150.00   26
 62  \w     79.00 105.00   1.00    8.00    --  105.88  77.00 120.00   26
 63  \w     16.00  65.00   1.00    2.00    --   34.73  38.00  90.00   49
 64  \w      8.00  50.00   1.00    2.00    --   34.73  77.00  30.00   42
 65  \w     10.00 100.00   1.00    2.00    --   34.73  77.00 -30.00   90
 66  \w     56.00  89.00   1.00    2.00    --   34.73  77.00-150.00   33
 67  \w     19.00  48.00   1.00    2.00    --   34.73  57.00-180.00   29
 68  \w      9.00  48.00   1.00    2.00    --   34.73  77.00-150.00   39
 69  \w     12.00  53.00   1.00    2.00    --   34.73  77.00-120.00   41
 70  \w     16.00  92.00   1.00    2.00    --   34.73  38.00 -60.00   76
 71  \w      8.00  53.00   1.00    2.00    --   34.73  77.00 -60.00   45
 72  \w     -1.00  25.00   1.00    2.00    --   34.73  95.00  91.31   26
 73  \w      8.00  92.00   1.00    2.00    --   34.73  77.00 120.00   84
 74  \w     -6.00  51.00   1.00    2.00    --   34.73 -38.00 150.00   57
 75  \w    -34.00  52.00   1.00    2.00    --   34.73 -38.00   0.00   86
 76  \w    -26.00  28.00   1.00    2.00    --   34.73 -57.00-120.00   54
 77  \w    -30.00  48.00   1.00    2.00    --   34.73 -38.00 -90.00   78
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, EosS2'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0498511000
_diffrn_orient_matrix_UB_12      0.0895415000
_diffrn_orient_matrix_UB_13      0.0481544000
_diffrn_orient_matrix_UB_21      -0.0833647000
_diffrn_orient_matrix_UB_22      0.0358242000
_diffrn_orient_matrix_UB_23      0.0069379000
_diffrn_orient_matrix_UB_31      -0.0132695000
_diffrn_orient_matrix_UB_32      -0.0145153000
_diffrn_orient_matrix_UB_33      0.0731581000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0444
_diffrn_reflns_av_unetI/netI     0.0381
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            68405
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        66.601
_diffrn_reflns_theta_max         66.601
_diffrn_reflns_theta_min         4.206
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    3.601
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.78275
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.46 (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            brown
_exptl_crystal_colour_primary    brown
_exptl_crystal_density_diffrn    1.353
_exptl_crystal_description       block
_exptl_crystal_F_000             2048
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.2
_refine_diff_density_max         0.698
_refine_diff_density_min         -0.710
_refine_diff_density_rms         0.063
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.016
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     1273
_refine_ls_number_reflns         17056
_refine_ls_number_restraints     30
_refine_ls_restrained_S_all      1.042
_refine_ls_R_factor_all          0.0820
_refine_ls_R_factor_gt           0.0645
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0980P)^2^+4.9875P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1724
_refine_ls_wR_factor_ref         0.1874
_reflns_Friedel_coverage         0.000
_reflns_number_gt                13291
_reflns_number_total             17056
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            19.cif
_cod_data_source_block           exp_666
_cod_depositor_comments
'Adding full bibliography for 4129104--4129109.cif.'
_cod_original_cell_volume        4844.8(3)
_cod_database_code               4129104
_shelx_shelxl_version_number     2016/6
_chemical_oxdiff_formula         'C50 N5 O2 H20 Cl3'
_shelx_estimated_absorpt_t_max   0.533
_shelx_estimated_absorpt_t_min   0.411
_reflns_odcompleteness_completeness 99.88
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.49
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 Cl6A-C103
 1.76 with sigma of 0.02
 Cl4A-C103
 1.76 with sigma of 0.02
 Cl5A-C103
 1.76 with sigma of 0.02
 Cl6A-Cl5A
 2.89 with sigma of 0.02
 Cl4A-Cl6A
 2.89 with sigma of 0.02
 Cl4A-Cl5A
 2.89 with sigma of 0.02
3. Uiso/Uaniso restraints and constraints
Uanis(Cl6A) \\sim Ueq, Uanis(Cl8A) \\sim Ueq, Uanis(Cl3) \\sim Ueq, Uanis(Cl9A)
\\sim Ueq: with sigma of 0.01 and sigma for terminal atoms of 0.02
4. Others
 Sof(HB)=Sof(Cl5A)=Sof(Cl4A)=Sof(Cl6A)=1-FVAR(1)
 Sof(Cl6)=Sof(HA)=Sof(Cl5)=Sof(Cl4)=FVAR(1)
 Sof(H3B)=Sof(Cl3A)=Sof(Cl1A)=Sof(Cl2A)=1-FVAR(2)
 Sof(Cl2)=Sof(Cl3)=Sof(Cl1)=Sof(H3A)=FVAR(2)
 Sof(H9JB)=Sof(Cl9A)=Sof(Cl8A)=Sof(Cl7A)=1-FVAR(3)
 Sof(Cl8)=Sof(Cl7)=Sof(Cl9)=Sof(H9JA)=FVAR(3)
5.a Ternary CH refined with riding coordinates:
 C102(H1), C104(H9JA), C104(H9JB), C103(HA), C103(HB), C101(H3A), C101(H3B)
5.b Aromatic/amide H refined with riding coordinates:
 N5(H4AA), N3(H5AA), N8(H9AA), N6(H1BA), C70(H9BA), C53(H6CA), C61(H8CA),
 C67(H9CA), C60(H3DA), C52(H5DA), C17(H8DA), C71(H9DA), C23(H0EA), C3(H1EA),
 C35(H3EA), C8(H4EA), C16(H8EA), C2(H1FA), C10(H3FA), C11(H4FA), C58(H5FA),
 C22(H6FA), C7(H2GA), C86(H8GA), C37(H0HA), C66(H2HA), C57(H6HA), C44(H7HA),
 C93(H8HA), C28(H4IA), C26(H5IA), C84(H6IA), C46(H4JA), C95(H6JA), C75(H4),
 C77(H2BA)
5.c Idealised Me refined as rotating group:
 C50(H1AA,H1AB,H1AC), C88(H2A,H2B,H2C), C40(H1HA,H1HB,H1HC), C31(H2IA,H2IB,
 H2IC), C41(H3IA,H3IB,H3IC), C90(H7IA,H7IB,H7IC), C30(H9IA,H9IB,H9IC), C99(H2JA,
 H2JB,H2JC), C48(H3JA,H3JB,H3JC), C39(H7JA,H7JB,H7JC), C97(H1KA,H1KB,H1KC),
 C32(H2KA,H2KB,H2KC), C89(H6KA,H6KB,H6KC), C49(H7KA,H7KB,H7KC), C98(H0LA,H0LB,
 H0LC), C80(H5A,H5B,H5C), C79(H7A,H7B,H7C), C81(H1BB,H1BC,H1BD)
;
_shelx_res_checksum              74681
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.355
_oxdiff_exptl_absorpt_empirical_full_min 0.725