#------------------------------------------------------------------------------
#$Date: 2022-05-05 22:40:35 +0200 (Thu 05 de May de 2022) $
#$Revision: 275000 $
#$URL: svn://www.crystallography.net/cod/cif/7/06/13/7061313.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_7061313
loop_
_publ_author_name
'Gharpure, Santosh J.'
'Jegadeesan, S.'
'Vishwakarma, Dharmendra S.'
_publ_section_title
;
 Total synthesis of myristinins A--F and
 3′-hydroxy-5,7-dimethoxy-4-O-2′-cycloflavan by iterative
 generation of o-quinone methides
;
_journal_issue                   12
_journal_name_full               'New Journal of Chemistry'
_journal_page_first              5460
_journal_page_last               5463
_journal_paper_doi               10.1039/D2NJ00244B
_journal_volume                  46
_journal_year                    2022
_chemical_formula_moiety         'C25 H23 Br O6'
_chemical_formula_sum            'C25 H24 Br O6'
_chemical_formula_weight         500.35
_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     dual
_audit_creation_date             2019-01-22
_audit_creation_method
;
Olex2 1.2-ac3
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381)
;
_audit_update_record
;
2021-07-16 deposited with the CCDC.	2022-02-21 downloaded from the CCDC.
;
_cell_angle_alpha                101.354(3)
_cell_angle_beta                 107.907(4)
_cell_angle_gamma                101.361(3)
_cell_formula_units_Z            2
_cell_length_a                   9.1036(4)
_cell_length_b                   9.9813(4)
_cell_length_c                   14.0392(6)
_cell_measurement_reflns_used    5742
_cell_measurement_temperature    150
_cell_measurement_theta_max      30.8720
_cell_measurement_theta_min      2.3500
_cell_volume                     1143.89(9)
_computing_cell_refinement
;
CrystalClear-SM Expert 2.0 r7 (Rigaku, 2011)
;
_computing_data_collection
;
CrystalClear-SM Expert 2.0 r7 (Rigaku, 2011)
;
_computing_data_reduction
;
CrystalClear-SM Expert 2.0 r7 (Rigaku, 2011)
;
_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    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      150
_diffrn_detector                 CCD
_diffrn_detector_area_resol_mean 28.5714
_diffrn_detector_type            'Rigaku Saturn724+'
_diffrn_measured_fraction_theta_full 0.976
_diffrn_measured_fraction_theta_max 0.976
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω   -110.00  70.00   0.50    8.00    --  -20.00   0.00 -36.00  360
  2  ω    -72.00  19.00   0.50    8.00    --  -20.00 -72.00 108.00  182
  3  ω    -69.00 -16.50   0.50    8.00    --  -20.00 -72.00 -36.00  105
;
_diffrn_measurement_device       'AFC12 (Right): Kappa 3 circle'
_diffrn_measurement_device_type  'Rigaku Saturn724+ (2x2 bin mode)'
_diffrn_measurement_method       'profile data from ω-scans'
_diffrn_measurement_specimen_support 'Mitegen 50um'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0328189000
_diffrn_orient_matrix_UB_12      -0.0581369000
_diffrn_orient_matrix_UB_13      -0.0084675000
_diffrn_orient_matrix_UB_21      -0.0342504000
_diffrn_orient_matrix_UB_22      -0.0107828000
_diffrn_orient_matrix_UB_23      -0.0545671000
_diffrn_orient_matrix_UB_31      0.0707626000
_diffrn_orient_matrix_UB_32      0.0468051000
_diffrn_orient_matrix_UB_33      0.0014720000
_diffrn_radiation_collimation    0.3
_diffrn_radiation_monochromator  Confocal
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0287
_diffrn_reflns_av_unetI/netI     0.0433
_diffrn_reflns_Laue_measured_fraction_full 0.976
_diffrn_reflns_Laue_measured_fraction_max 0.976
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            7129
_diffrn_reflns_point_group_measured_fraction_full 0.976
_diffrn_reflns_point_group_measured_fraction_max 0.976
_diffrn_reflns_theta_full        24.996
_diffrn_reflns_theta_max         24.996
_diffrn_reflns_theta_min         2.784
_diffrn_source                   'Rotating Anode'
_diffrn_source_current           24.0
_diffrn_source_power             1.2
_diffrn_source_target            Mo
_diffrn_source_type              'Rotating Anode'
_diffrn_source_voltage           50.0
_exptl_absorpt_coefficient_mu    1.835
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.44550
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.46 (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.453
_exptl_crystal_description       block
_exptl_crystal_F_000             514
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.294
_refine_diff_density_min         -0.290
_refine_diff_density_rms         0.071
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.002
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     292
_refine_ls_number_reflns         3932
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.002
_refine_ls_R_factor_all          0.0430
_refine_ls_R_factor_gt           0.0344
_refine_ls_shift/su_max          0.008
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0379P)²+0.5256P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0767
_refine_ls_wR_factor_ref         0.0817
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3430
_reflns_number_total             3932
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d2nj00244b2.cif
_cod_data_source_block           sjg-jsm-06-35_mo
_cod_depositor_comments
'Adding full bibliography for 7061308--7061314.cif.'
_cod_original_cell_volume        1143.89(8)
_cod_database_code               7061313
_shelx_shelxl_version_number     2018/3
_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_max   0.867
_shelx_estimated_absorpt_t_min   0.734
_reflns_odcompleteness_completeness 84.18
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     30.97
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C9(H9), C17(H17)
2.b Secondary CH2 refined with riding coordinates:
 C18(H18A,H18B), C25(H25A,H25B)
2.c Aromatic/amide H refined with riding coordinates:
 C3(H3), C20(H20), C24(H24), C23(H23), C15(H15), C14(H14), C12(H12), C5(H5)
2.d Idealised Me refined as rotating group:
 C1(H1A,H1B,H1C), C10(H10A,H10B,H10C), C8(H8A,H8B,H8C)
;
_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
- Detector area scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.756
_oxdiff_exptl_absorpt_empirical_full_min 0.583
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
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Br1 Br 1.13222(3) 0.88405(3) 0.25030(2) 0.03144(11) Uani 1 1 d . . . . .
O4 O 0.49818(18) 0.46200(16) 0.15925(15) 0.0242(4) Uani 1 1 d . . . . .
O5 O 0.0993(2) 0.26234(19) 0.33056(15) 0.0292(4) Uani 1 1 d . . . . .
O3 O 0.6270(2) 0.81092(19) 0.37386(14) 0.0288(4) Uani 1 1 d . . . . .
O2 O 0.41728(19) 0.98603(16) 0.09163(14) 0.0220(4) Uani 1 1 d . . . . .
O6 O -0.1435(2) 0.15732(19) 0.19470(15) 0.0287(4) Uani 1 1 d . . . . .
O1 O 0.6202(3) 1.30579(19) 0.42979(17) 0.0412(5) Uani 1 1 d . . . . .
C22 C -0.0349(3) 0.2314(2) 0.1600(2) 0.0214(6) Uani 1 1 d . . . . .
C3 C 0.5183(3) 1.1487(3) 0.2644(2) 0.0230(6) Uani 1 1 d . . . . .
H3 H 0.489895 1.224348 0.237957 0.028 Uiso 1 1 calc R . . . .
C16 C 0.6375(3) 0.5623(2) 0.1765(2) 0.0195(5) Uani 1 1 d . . . . .
C21 C 0.1103(3) 0.2950(2) 0.2417(2) 0.0204(5) Uani 1 1 d . . . . .
C19 C 0.2184(3) 0.3936(2) 0.1295(2) 0.0210(6) Uani 1 1 d . . . . .
C20 C 0.2393(3) 0.3753(2) 0.2287(2) 0.0215(6) Uani 1 1 d . . . . .
H20 H 0.339164 0.417095 0.284896 0.026 Uiso 1 1 calc R . . . .
C18 C 0.3597(3) 0.6472(2) 0.1669(2) 0.0209(6) Uani 1 1 d . . . . .
H18A H 0.375923 0.656470 0.241156 0.025 Uiso 1 1 calc R . . . .
H18B H 0.256514 0.667465 0.134135 0.025 Uiso 1 1 calc R . . . .
C9 C 0.4964(3) 0.7575(2) 0.1595(2) 0.0167(5) Uani 1 1 d . . . . .
H9 H 0.461927 0.767581 0.087059 0.020 Uiso 1 1 calc R . . . .
C11 C 0.6459(3) 0.7037(2) 0.17810(19) 0.0166(5) Uani 1 1 d . . . . .
C24 C 0.0728(3) 0.3287(3) 0.0484(2) 0.0243(6) Uani 1 1 d . . . . .
H24 H 0.061254 0.341065 -0.018680 0.029 Uiso 1 1 calc R . . . .
C17 C 0.3493(3) 0.4963(2) 0.1146(2) 0.0215(6) Uani 1 1 d . . . . .
H17 H 0.325081 0.484356 0.038510 0.026 Uiso 1 1 calc R . . . .
C23 C -0.0577(3) 0.2454(3) 0.0621(2) 0.0260(6) Uani 1 1 d . . . . .
H23 H -0.157188 0.200726 0.006074 0.031 Uiso 1 1 calc R . . . .
C4 C 0.5900(3) 1.1698(3) 0.3697(2) 0.0256(6) Uani 1 1 d . . . . .
C2 C 0.4876(3) 1.0162(2) 0.1970(2) 0.0175(5) Uani 1 1 d . . . . .
C25 C -0.0681(3) 0.2018(3) 0.3055(2) 0.0318(7) Uani 1 1 d . . . . .
H25A H -0.084907 0.119455 0.334201 0.038 Uiso 1 1 calc R . . . .
H25B H -0.114909 0.273043 0.335845 0.038 Uiso 1 1 calc R . . . .
C7 C 0.5287(3) 0.9022(2) 0.23407(19) 0.0163(5) Uani 1 1 d . . . . .
C15 C 0.7760(3) 0.5159(3) 0.1960(2) 0.0252(6) Uani 1 1 d . . . . .
H15 H 0.768473 0.418951 0.193812 0.030 Uiso 1 1 calc R . . . .
C1 C 0.3634(3) 1.0951(3) 0.0497(2) 0.0334(7) Uani 1 1 d . . . . .
H1A H 0.313065 1.059102 -0.026228 0.050 Uiso 1 1 calc GR . . . .
H1B H 0.455337 1.177891 0.068205 0.050 Uiso 1 1 calc GR . . . .
H1C H 0.285114 1.122720 0.078630 0.050 Uiso 1 1 calc GR . . . .
C14 C 0.9240(3) 0.6093(3) 0.2183(2) 0.0260(6) Uani 1 1 d . . . . .
H14 H 1.018589 0.578065 0.233053 0.031 Uiso 1 1 calc R . . . .
C12 C 0.7942(3) 0.7958(3) 0.19812(19) 0.0194(5) Uani 1 1 d . . . . .
H12 H 0.801759 0.891966 0.197652 0.023 Uiso 1 1 calc R . . . .
C5 C 0.6301(3) 1.0595(3) 0.4112(2) 0.0262(6) Uani 1 1 d . . . . .
H5 H 0.678593 1.074284 0.484186 0.031 Uiso 1 1 calc R . . . .
C6 C 0.5962(3) 0.9275(3) 0.3414(2) 0.0212(6) Uani 1 1 d . . . . .
C10 C 0.7192(4) 0.8305(3) 0.4800(2) 0.0433(8) Uani 1 1 d . . . . .
H10A H 0.737546 0.739884 0.490062 0.065 Uiso 1 1 calc GR . . . .
H10B H 0.661063 0.864204 0.523829 0.065 Uiso 1 1 calc GR . . . .
H10C H 0.822662 0.900817 0.499488 0.065 Uiso 1 1 calc GR . . . .
C13 C 0.9312(3) 0.7496(3) 0.2187(2) 0.0215(5) Uani 1 1 d . . . . .
C8 C 0.7117(5) 1.3396(3) 0.5375(3) 0.0554(9) Uani 1 1 d . . . . .
H8A H 0.814521 1.317316 0.546670 0.083 Uiso 1 1 calc GR . . . .
H8B H 0.652474 1.283638 0.570812 0.083 Uiso 1 1 calc GR . . . .
H8C H 0.731520 1.441086 0.569552 0.083 Uiso 1 1 calc GR . . . .
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'
Br Br -0.2901 2.4595 '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
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C16 O4 C17 116.79(17) . . ?
C21 O5 C25 104.74(19) . . ?
C6 O3 C10 118.9(2) . . ?
C2 O2 C1 117.7(2) . . ?
C22 O6 C25 104.39(18) . . ?
C4 O1 C8 118.1(2) . . ?
O6 C22 C21 109.7(2) . . ?
C23 C22 O6 128.3(2) . . ?
C23 C22 C21 121.9(2) . . ?
C4 C3 H3 120.3 . . ?
C4 C3 C2 119.5(2) . . ?
C2 C3 H3 120.3 . . ?
O4 C16 C11 123.7(2) . . ?
O4 C16 C15 115.9(2) . . ?
C15 C16 C11 120.4(2) . . ?
O5 C21 C22 109.4(2) . . ?
C20 C21 O5 128.7(2) . . ?
C20 C21 C22 121.9(2) . . ?
C20 C19 C17 119.3(2) . . ?
C24 C19 C20 120.1(2) . . ?
C24 C19 C17 120.2(2) . . ?
C21 C20 C19 117.4(2) . . ?
C21 C20 H20 121.3 . . ?
C19 C20 H20 121.3 . . ?
H18A C18 H18B 107.8 . . ?
C9 C18 H18A 109.0 . . ?
C9 C18 H18B 109.0 . . ?
C17 C18 H18A 109.0 . . ?
C17 C18 H18B 109.0 . . ?
C17 C18 C9 113.0(2) . . ?
C18 C9 H9 107.9 . . ?
C11 C9 C18 109.66(18) . . ?
C11 C9 H9 107.9 . . ?
C7 C9 C18 111.13(19) . . ?
C7 C9 H9 107.9 . . ?
C7 C9 C11 112.31(19) . . ?
C16 C11 C9 121.2(2) . . ?
C12 C11 C16 118.4(2) . . ?
C12 C11 C9 120.4(2) . . ?
C19 C24 H24 119.0 . . ?
C19 C24 C23 122.0(2) . . ?
C23 C24 H24 119.0 . . ?
O4 C17 C19 107.59(18) . . ?
O4 C17 C18 111.0(2) . . ?
O4 C17 H17 109.4 . . ?
C19 C17 C18 110.1(2) . . ?
C19 C17 H17 109.4 . . ?
C18 C17 H17 109.4 . . ?
C22 C23 C24 116.6(2) . . ?
C22 C23 H23 121.7 . . ?
C24 C23 H23 121.7 . . ?
O1 C4 C3 115.1(2) . . ?
O1 C4 C5 123.3(3) . . ?
C3 C4 C5 121.6(2) . . ?
O2 C2 C3 123.4(2) . . ?
O2 C2 C7 115.1(2) . . ?
C3 C2 C7 121.4(2) . . ?
O5 C25 H25A 110.1 . . ?
O5 C25 H25B 110.1 . . ?
O6 C25 O5 107.9(2) . . ?
O6 C25 H25A 110.1 . . ?
O6 C25 H25B 110.1 . . ?
H25A C25 H25B 108.4 . . ?
C2 C7 C9 121.2(2) . . ?
C6 C7 C9 121.9(2) . . ?
C6 C7 C2 116.9(2) . . ?
C16 C15 H15 119.6 . . ?
C14 C15 C16 120.8(2) . . ?
C14 C15 H15 119.6 . . ?
O2 C1 H1A 109.5 . . ?
O2 C1 H1B 109.5 . . ?
O2 C1 H1C 109.5 . . ?
H1A C1 H1B 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
C15 C14 H14 120.8 . . ?
C15 C14 C13 118.5(2) . . ?
C13 C14 H14 120.8 . . ?
C11 C12 H12 119.5 . . ?
C13 C12 C11 120.9(2) . . ?
C13 C12 H12 119.5 . . ?
C4 C5 H5 121.3 . . ?
C6 C5 C4 117.4(3) . . ?
C6 C5 H5 121.3 . . ?
O3 C6 C7 114.6(2) . . ?
O3 C6 C5 122.3(2) . . ?
C7 C6 C5 123.1(2) . . ?
O3 C10 H10A 109.5 . . ?
O3 C10 H10B 109.5 . . ?
O3 C10 H10C 109.5 . . ?
H10A C10 H10B 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C14 C13 Br1 120.45(17) . . ?
C12 C13 Br1 118.53(18) . . ?
C12 C13 C14 121.0(2) . . ?
O1 C8 H8A 109.5 . . ?
O1 C8 H8B 109.5 . . ?
O1 C8 H8C 109.5 . . ?
H8A C8 H8B 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Br1 C13 1.909(2) . ?
O4 C16 1.373(3) . ?
O4 C17 1.446(3) . ?
O5 C21 1.378(3) . ?
O5 C25 1.427(3) . ?
O3 C6 1.378(3) . ?
O3 C10 1.420(3) . ?
O2 C2 1.362(3) . ?
O2 C1 1.434(3) . ?
O6 C22 1.383(3) . ?
O6 C25 1.428(3) . ?
O1 C4 1.374(3) . ?
O1 C8 1.417(4) . ?
C22 C21 1.384(3) . ?
C22 C23 1.366(4) . ?
C3 H3 0.9500 . ?
C3 C4 1.374(4) . ?
C3 C2 1.386(3) . ?
C16 C11 1.394(3) . ?
C16 C15 1.395(3) . ?
C21 C20 1.368(3) . ?
C19 C20 1.400(4) . ?
C19 C24 1.384(4) . ?
C19 C17 1.507(3) . ?
C20 H20 0.9500 . ?
C18 H18A 0.9900 . ?
C18 H18B 0.9900 . ?
C18 C9 1.535(3) . ?
C18 C17 1.510(3) . ?
C9 H9 1.0000 . ?
C9 C11 1.527(3) . ?
C9 C7 1.522(3) . ?
C11 C12 1.387(3) . ?
C24 H24 0.9500 . ?
C24 C23 1.398(3) . ?
C17 H17 1.0000 . ?
C23 H23 0.9500 . ?
C4 C5 1.402(4) . ?
C2 C7 1.410(3) . ?
C25 H25A 0.9900 . ?
C25 H25B 0.9900 . ?
C7 C6 1.390(4) . ?
C15 H15 0.9500 . ?
C15 C14 1.383(3) . ?
C1 H1A 0.9800 . ?
C1 H1B 0.9800 . ?
C1 H1C 0.9800 . ?
C14 H14 0.9500 . ?
C14 C13 1.389(3) . ?
C12 H12 0.9500 . ?
C12 C13 1.381(3) . ?
C5 H5 0.9500 . ?
C5 C6 1.392(4) . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 0.9800 . ?
C8 H8A 0.9800 . ?
C8 H8B 0.9800 . ?
C8 H8C 0.9800 . ?
