The Leaving Group Strongly Affects H2O2-Induced DNA Cross-Linking by Arylboronates.
Cao, Sheng; Wang, Yibin; Peng, Xiaohua; The Journal of organic chemistry 79 (2014) 501–508; doi:10.1021/jo401901x

data_4028981
_publ_section_title
;
 The Leaving Group Strongly Affects H2O2-Induced DNA Cross-Linking by
 Arylboronates.
;
_journal_issue                   2
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              501
_journal_page_last               508
_journal_paper_doi               10.1021/jo401901x
_journal_volume                  79
_journal_year                    2014
_chemical_formula_moiety         'C26 H34 B2 Br2 O4'
_chemical_formula_sum            'C26 H34 B2 Br2 O4'
_chemical_formula_weight         591.97
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_date             2013-03-20
_audit_creation_method
;
  Olex2 1.2
  (compiled Dec  5 2012 16:20:19, GUI svn.r4385)
;
_cell_angle_alpha                90.00
_cell_angle_beta                 100.2067(16)
_cell_angle_gamma                90.00
_cell_formula_units_Z            16
_cell_length_a                   19.0571(3)
_cell_length_b                   26.6288(4)
_cell_length_c                   22.2563(4)
_cell_measurement_reflns_used    24432
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      73.9637
_cell_measurement_theta_min      3.2673
_cell_volume                     11115.6(3)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.15 (release 03-08-2011 CrysAlis171 .NET)
(compiled Aug  3 2011,13:03:54)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.15 (release 03-08-2011 CrysAlis171 .NET)
(compiled Aug  3 2011,13:03:54)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.15 (release 03-08-2011 CrysAlis171 .NET)
(compiled Aug  3 2011,13:03:54)
;
_computing_molecular_graphics
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_publication_material
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_structure_refinement
;
XL, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      100.00(10)
_diffrn_detector_area_resol_mean 10.3756
_diffrn_measured_fraction_theta_full 0.990
_diffrn_measured_fraction_theta_max 0.974
_diffrn_measurement_details
;
  1 omega  -95.00  -18.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      -40.3987  125.0000    0.0000 77

  2 omega -119.00  -23.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      -40.3987  -77.0000 -120.0000 96

  3 omega   70.00   95.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -       40.3987  162.0000  103.0000 25

  4 omega   10.00   41.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -       40.3987   19.0000  -90.0000 31

  5 omega   89.00  115.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -       40.3987   19.0000  -90.0000 26

  6 omega   85.00  153.00   1.0000   40.0000
omega____ theta____ kappa____ phi______ frames
    -      107.0378   77.0000  -30.0000 68

  7 omega   59.00   91.00   1.0000   40.0000
omega____ theta____ kappa____ phi______ frames
    -      107.0378  -30.0000  150.0000 32

  8 omega   47.00   87.00   1.0000   40.0000
omega____ theta____ kappa____ phi______ frames
    -      107.0378  -30.0000   30.0000 40

  9 omega   52.00  109.00   1.0000   40.0000
omega____ theta____ kappa____ phi______ frames
    -      107.0378  -94.0000 -120.0000 57

 10 omega   95.00  178.00   1.0000   40.0000
omega____ theta____ kappa____ phi______ frames
    -      107.0378  125.0000  -30.0000 83

 11 omega  146.00  178.00   1.0000   40.0000
omega____ theta____ kappa____ phi______ frames
    -      107.0378  125.0000   90.0000 32

 12 omega   78.00  168.00   1.0000   40.0000
omega____ theta____ kappa____ phi______ frames
    -      107.0378   30.0000  -60.0000 90

 13 omega   37.00   99.00   1.0000   40.0000
omega____ theta____ kappa____ phi______ frames
    -      107.0378  -45.0000 -120.0000 62

 14 omega -114.00  -11.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      -40.3987  -57.0000   60.0000 103

 15 omega  -49.00   36.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      -40.3987   37.0000    0.0000 85

 16 omega -119.00   -7.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      -40.3987  -77.0000  -30.0000 112

 17 omega   46.00   71.00   1.0000   40.0000
omega____ theta____ kappa____ phi______ frames
    -      107.0378   15.0000  150.0000 25

 18 omega   29.00   91.00   1.0000   40.0000
omega____ theta____ kappa____ phi______ frames
    -      107.0378  -30.0000  -30.0000 62
;
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      -0.0422923000
_diffrn_orient_matrix_UB_12      -0.0001972000
_diffrn_orient_matrix_UB_13      -0.0657881000
_diffrn_orient_matrix_UB_21      -0.0101296000
_diffrn_orient_matrix_UB_22      0.0572259000
_diffrn_orient_matrix_UB_23      0.0034133000
_diffrn_orient_matrix_UB_31      0.0697176000
_diffrn_orient_matrix_UB_32      0.0083188000
_diffrn_orient_matrix_UB_33      -0.0246725000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.5418
_diffrn_reflns_av_R_equivalents  0.0366
_diffrn_reflns_av_unetI/netI     0.0317
_diffrn_reflns_limit_h_max       23
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       32
_diffrn_reflns_limit_k_min       -30
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_number            68428
_diffrn_reflns_theta_full        72.00
_diffrn_reflns_theta_max         74.13
_diffrn_reflns_theta_min         3.27
_diffrn_source                   'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    3.924
_exptl_absorpt_correction_T_max  0.729
_exptl_absorpt_correction_T_min  0.435
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.15 (release 03-08-2011 CrysAlis171 .NET)
(compiled Aug  3 2011,13:03:54)
Numerical absorption correction based on gaussian integration over
            a multifaceted crystal model
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.415
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             4832
_exptl_crystal_size_max          0.3817
_exptl_crystal_size_mid          0.1615
_exptl_crystal_size_min          0.1099
_refine_diff_density_max         3.492
_refine_diff_density_min         -1.215
_refine_diff_density_rms         0.140
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.067
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     1257
_refine_ls_number_reflns         22035
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.067
_refine_ls_R_factor_all          0.0811
_refine_ls_R_factor_gt           0.0743
_refine_ls_shift/su_max          0.004
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.1022P)^2^+50.8993P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1982
_refine_ls_wR_factor_ref         0.2044
_reflns_number_gt                19184
_reflns_number_total             22035
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo401901x_si_003.cif
_cod_data_source_block           uwm1f
_cod_database_code               4028981
_chemical_oxdiff_formula         'Br2 O4 B2 C26 H34'
_reflns_odcompleteness_completeness 99.94
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_olex2_refinement_description
;
1. Others
 Fixed Uiso: H2(0.028) H5(0.032) H6(0.033) H7A(0.038) H7B(0.038) H10D(0.059)
 H10E(0.059) H10F(0.059) H11D(0.062) H11E(0.062) H11F(0.062) H12D(0.054)
 H12E(0.054) H12F(0.054) H13D(0.058) H13E(0.058) H13F(0.058) H15(0.027)
 H18(0.029) H19(0.03) H20C(0.031) H20D(0.031) H23D(0.053) H23E(0.053)
 H23F(0.053) H24D(0.062) H24E(0.062) H24F(0.062) H25D(0.051) H25E(0.051)
 H25F(0.051) H26D(0.062) H26E(0.062) H26F(0.062) H2A(0.029) H5A(0.031)
 H6A(0.031) H7AA(0.035) H7AB(0.035) H10G(0.062) H10H(0.062) H10I(0.062)
 H11G(0.063) H11H(0.063) H11I(0.063) H12G(0.067) H12H(0.067) H12I(0.067)
 H13G(0.061) H13H(0.061) H13I(0.061) H15A(0.03) H18A(0.031) H19A(0.03)
 H20E(0.033) H20F(0.033) H23G(0.064) H23H(0.064) H23I(0.064) H24G(0.053)
 H24H(0.053) H24I(0.053) H25G(0.062) H25H(0.062) H25I(0.062) H26G(0.054)
 H26H(0.054) H26I(0.054) H2B(0.028) H5B(0.032) H6B(0.03) H7BA(0.031)
 H7BB(0.031) H10J(0.074) H10K(0.074) H10L(0.074) H11J(0.082) H11K(0.082)
 H11L(0.082) H12J(0.068) H12K(0.068) H12L(0.068) H13J(0.077) H13K(0.077)
 H13L(0.077) H15B(0.029) H18B(0.031) H19B(0.03) H20G(0.035) H20H(0.035)
 H23J(0.075) H23K(0.075) H23L(0.075) H24J(0.064) H24K(0.064) H24L(0.064)
 H25J(0.074) H25K(0.074) H25L(0.074) H26J(0.071) H26K(0.071) H26L(0.071)
 H2C(0.029) H5C(0.032) H6C(0.031) H7CA(0.034) H7CB(0.034) H10A(0.06) H10B(0.06)
 H10C(0.06) H11A(0.059) H11B(0.059) H11C(0.059) H12A(0.061) H12B(0.061)
 H12C(0.061) H13A(0.058) H13B(0.058) H13C(0.058) H15C(0.028) H18C(0.033)
 H19C(0.033) H20A(0.034) H20B(0.034) H23A(0.095) H23B(0.095) H23C(0.095)
 H24A(0.089) H24B(0.089) H24C(0.089) H25A(0.096) H25B(0.096) H25C(0.096)
 H26A(0.078) H26B(0.078) H26C(0.078)
 Fixed X: H2(0.7065) H5(0.5939) H6(0.6833) H7A(0.6087) H7B(0.6594)
 H10D(0.3909) H10E(0.3902) H10F(0.3403) H11D(0.4832) H11E(0.4383) H11F(0.3981)
 H12D(0.3626) H12E(0.3908) H12F(0.3486) H13D(0.4941) H13E(0.5414) H13F(0.4686)
 H15(0.8091) H18(0.7845) H19(0.7162) H20C(0.9494) H20D(0.9173) H23D(0.8727)
 H23E(0.9382) H23F(0.9508) H24D(0.8567) H24E(0.8313) H24F(0.909) H25D(1.0413)
 H25E(1.0746) H25F(1.0454) H26D(0.9957) H26E(0.9134) H26F(0.9739) H2A(0.1185)
 H5A(0.0212) H6A(0.1078) H7AA(0.0692) H7AB(0.0219) H10G(-0.1109) H10H(-0.1956)
 H10I(-0.1529) H11G(-0.1952) H11H(-0.2463) H11I(-0.1939) H12G(-0.0809) H12H(-
 0.1289) H12I(-0.0536) H13G(-0.2183) H13H(-0.2352) H13I(-0.1885) H15A(0.2296)
 H18A(0.1921) H19A(0.1272) H20E(0.3359) H20F(0.3625) H23G(0.3976) H23H(0.3731)
 H23I(0.3148) H24G(0.4499) H24H(0.4493) H24I(0.4795) H25G(0.2556) H25H(0.31)
 H25I(0.2348) H26G(0.2809) H26H(0.3582) H26I(0.3466) H2B(0.7893) H5B(0.5461)
 H6B(0.5874) H7BA(0.8143) H7BB(0.7519) H10J(0.565) H10K(0.5512) H10L(0.6308)
 H11J(0.6542) H11K(0.5743) H11L(0.6281) H12J(0.4132) H12K(0.4467) H12L(0.4525)
 H13J(0.5649) H13K(0.5029) H13L(0.4833) H15B(0.6226) H18B(0.8659) H19B(0.8261)
 H20G(0.5938) H20H(0.6541) H23J(0.7515) H23K(0.8346) H23L(0.8072) H24J(0.7857)
 H24K(0.8219) H24L(0.7401) H25J(0.9357) H25K(0.9468) H25L(0.9885) H26J(0.9413)
 H26K(0.9172) H26L(0.8604) H2C(0.2079) H5C(0.1666) H6C(0.282) H7CA(0.0288)
 H7CB(0.0872) H10A(-0.1598) H10B(-0.1283) H10C(-0.1812) H11A(-0.0592) H11B(-
 0.1142) H11C(-0.1401) H12A(-0.0299) H12B(-0.0076) H12C(-0.0901) H13A(-0.0436)
 H13B(-0.06) H13C(-0.1202) H15C(0.3797) H18C(0.4277) H19C(0.3107) H20A(0.5585)
 H20B(0.4983) H23A(0.6387) H23B(0.6633) H23C(0.717) H24A(0.6328) H24B(0.6033)
 H24C(0.6874) H25A(0.656) H25B(0.6971) H25C(0.7387) H26A(0.7485) H26B(0.7226)
 H26C(0.7748)
 Fixed Y: H2(0.3043) H5(0.4603) H6(0.4459) H7A(0.3195) H7B(0.282) H10D(0.3332)
 H10E(0.3745) H10F(0.3814) H11D(0.4046) H11E(0.3542) H11F(0.407) H12D(0.4595)
 H12E(0.5126) H12F(0.476) H13D(0.5209) H13E(0.4737) H13F(0.4857) H15(0.4289)
 H18(0.2837) H19(0.2939) H20C(0.4128) H20D(0.4485) H23D(0.2339) H23E(0.2472)
 H23F(0.2414) H24D(0.3533) H24E(0.296) H24F(0.3115) H25D(0.2883) H25E(0.3433)
 H25F(0.314) H26D(0.4172) H26E(0.4088) H26F(0.3934) H2A(0.6978) H5A(0.5369)
 H6A(0.5543) H7AA(0.7187) H7AB(0.6792) H10G(0.5836) H10H(0.5832) H10I(0.6352)
 H11G(0.6593) H11H(0.6112) H11I(0.6188) H12G(0.4739) H12H(0.4961) H12I(0.5213)
 H13G(0.5361) H13H(0.5139) H13I(0.482) H15A(0.5759) H18A(0.7191) H19A(0.7078)
 H20E(0.5588) H20F(0.5932) H23G(0.5881) H23H(0.6131) H23I(0.5978) H24G(0.7146)
 H24H(0.692) H24I(0.6592) H25G(0.656) H25H(0.6955) H25I(0.7142) H26G(0.7741)
 H26H(0.7653) H26I(0.7595) H2B(0.678) H5B(0.6858) H6B(0.6922) H7BA(0.6902)
 H7BB(0.6858) H10J(0.7556) H10K(0.7455) H10L(0.7532) H11J(0.674) H11K(0.6551)
 H11L(0.6218) H12J(0.6678) H12K(0.682) H12L(0.7206) H13J(0.5889) H13K(0.5944)
 H13L(0.5909) H15B(0.6773) H18B(0.6893) H19B(0.6928) H20G(0.6853) H20H(0.6891)
 H23J(0.6129) H23K(0.6087) H23L(0.5983) H24J(0.7413) H24K(0.7017) H24L(0.6953)
 H25J(0.6198) H25K(0.658) H25L(0.6666) H26J(0.7492) H26K(0.7498) H26L(0.762)
 H2C(0.4405) H5C(0.4548) H6C(0.4581) H7CA(0.456) H7CB(0.4496) H10A(0.4318)
 H10B(0.3812) H10C(0.4155) H11A(0.5189) H11B(0.5148) H11C(0.5026) H12A(0.3533)
 H12B(0.3518) H12C(0.3521) H13A(0.4228) H13B(0.4766) H13C(0.434) H15C(0.432)
 H18C(0.4586) H19C(0.4596) H20A(0.4492) H20B(0.4387) H23A(0.4282) H23B(0.4806)
 H23C(0.4339) H24A(0.356) H24B(0.3563) H24C(0.3571) H25A(0.5206) H25B(0.5174)
 H25C(0.5056) H26A(0.4374) H26B(0.3858) H26C(0.4224)
 Fixed Z: H2(0.2538) H5(0.2445) H6(0.1882) H7A(0.3694) H7B(0.3403)
 H10D(0.3443) H10E(0.292) H10F(0.3421) H11D(0.4679) H11E(0.4505) H11F(0.4506)
 H12D(0.289) H12E(0.317) H12F(0.3551) H13D(0.3911) H13E(0.4179) H13F(0.4415)
 H15(0.1866) H18(0.0677) H19(0.1439) H20C(0.1093) H20D(0.1556) H23D(-0.0613)
 H23E(-0.0081) H23F(-0.077) H24D(-0.1345) H24E(-0.1422) H24F(-0.1536) H25D(-
 0.0096) H25E(-0.0117) H25F(-0.0739) H26D(-0.0353) H26E(-0.064) H26F(-0.1021)
 H2A(0.71) H5A(0.7058) H6A(0.6478) H7AA(0.7962) H7AB(0.826) H10G(0.9177)
 H10H(0.896) H10I(0.9011) H11G(0.7939) H11H(0.7891) H11I(0.741) H12G(0.8341)
 H12H(0.88) H12I(0.8761) H13G(0.732) H13H(0.7947) H13I(0.7553) H15A(0.6433)
 H18A(0.5212) H19A(0.5997) H20E(0.6085) H20F(0.558) H23G(0.4096) H23H(0.3438)
 H23I(0.3841) H24G(0.4397) H24H(0.373) H24I(0.4322) H25G(0.3175) H25H(0.2969)
 H25I(0.3111) H26G(0.391) H26H(0.3743) H26I(0.4434) H2B(0.1677) H5B(0.0929)
 H6B(0.197) H7BA(0.0672) H7BB(0.0087) H10J(-0.0846) H10K(-0.1566) H10L(-0.1203)
 H11J(-0.1699) H11K(-0.1932) H11L(-0.146) H12J(-0.1004) H12K(-0.1592) H12L(-
 0.1034) H13J(-0.0758) H13K(-0.1341) H13L(-0.0673) H15B(0.2858) H18B(0.3643)
 H19B(0.259) H20G(0.3828) H20H(0.4428) H23J(0.5839) H23K(0.6119) H23L(0.5407)
 H24J(0.5999) H24K(0.65) H24L(0.6188) H25J(0.5657) H25K(0.6222) H25L(0.5666)
 H26J(0.531) H26K(0.5963) H26L(0.536) H2C(0.827) H5C(0.6155) H6C(0.6682)
 H7CA(0.7694) H7CB(0.8304) H10A(0.6647) H10B(0.6413) H10C(0.5946) H11A(0.5934)
 H11B(0.6398) H11C(0.569) H12A(0.6099) H12B(0.5439) H12C(0.5499) H13A(0.4731)
 H13B(0.4996) H13C(0.4902) H15C(0.7151) H18C(0.9247) H19C(0.8736) H20A(0.7661)
 H20B(0.7072) H23A(1.0595) H23B(1.0348) H23C(1.0435) H24A(0.9279) H24B(0.9909)
 H24C(0.9914) H25A(0.9424) H25B(0.8858) H25C(0.9533) H26A(0.8645) H26B(0.8902)
 H26C(0.9344)
;