#------------------------------------------------------------------------------
#$Date: 2017-01-09 06:31:42 +0200 (Mon, 09 Jan 2017) $
#$Revision: 190226 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/11/91/7119184.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_7119184
loop_
_publ_author_name
'Herdman, Christine A.'
'Strecker, Tracy E.'
'Tanpure, Rajendra P.'
'Chen, Zhi'
'Winters, Alex'
'Gerberich, Jeni'
'Liu, Li'
'Hamel, Ernest'
'Mason, Ralph P.'
'Chaplin, David J.'
'Trawick, Mary Lynn'
'Pinney, Kevin G.'
_publ_section_title
;
 Synthesis and biological evaluation of benzocyclooctene-based and
 indene-based anticancer agents that function as inhibitors of tubulin
 polymerization
;
_journal_issue                   12
_journal_name_full               'Med. Chem. Commun.'
_journal_page_first              2418
_journal_paper_doi               10.1039/C6MD00459H
_journal_volume                  7
_journal_year                    2016
_chemical_formula_sum            'C23 H28 O5'
_chemical_formula_weight         384.45
_chemical_name_systematic
; 
 ? 
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2014
_audit_update_record
;
2015-01-29 deposited with the CCDC.
2016-09-20 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 102.544(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   11.7350(5)
_cell_length_b                   9.4232(5)
_cell_length_c                   18.5619(10)
_cell_measurement_reflns_used    5525
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      29.62
_cell_measurement_theta_min      2.44
_cell_volume                     2003.60(17)
_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-2014 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_diffrn_ambient_temperature      150(2)
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0336
_diffrn_reflns_av_unetI/netI     0.0564
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            13077
_diffrn_reflns_point_group_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.679
_diffrn_reflns_theta_min         2.436
_exptl_absorpt_coefficient_mu    0.089
_exptl_absorpt_correction_T_max  0.902
_exptl_absorpt_correction_T_min  0.885
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.275
_exptl_crystal_description       Plate
_exptl_crystal_F_000             824
_exptl_crystal_size_max          0.257
_exptl_crystal_size_mid          0.138
_exptl_crystal_size_min          0.039
_refine_diff_density_max         0.344
_refine_diff_density_min         -0.242
_refine_diff_density_rms         0.050
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.025
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     253
_refine_ls_number_reflns         5627
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.025
_refine_ls_R_factor_all          0.0879
_refine_ls_R_factor_gt           0.0541
_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/[σ²(Fo²)+(0.0500P)²+0.7356P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1131
_refine_ls_wR_factor_ref         0.1267
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3948
_reflns_number_total             5627
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            c6md00459h2.cif
_cod_data_source_block           KP75
_cod_depositor_comments
'Adding full bibliography for 7119184--7119185.cif.'
_cod_database_code               7119184
_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_min   0.978
_shelx_estimated_absorpt_t_max   0.997
_shelxl_version_number           2014-3
loop_
_space_group_symop_operation_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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
O1 O 0.31726(10) 1.43828(12) 0.40249(6) 0.0302(3) Uani 1 1 d . .
O2 O 0.48607(9) 1.33573(12) 0.34121(6) 0.0288(3) Uani 1 1 d . .
O3 O 0.08573(9) 0.94968(12) 0.07705(6) 0.0279(3) Uani 1 1 d . .
O4 O 0.02511(8) 0.67695(11) 0.05890(5) 0.0233(2) Uani 1 1 d . .
O5 O 0.08192(9) 0.48986(11) 0.16996(6) 0.0267(2) Uani 1 1 d . .
C1 C 0.31803(12) 1.00927(16) 0.34809(7) 0.0198(3) Uani 1 1 d . .
C2 C 0.22722(12) 1.06428(17) 0.37672(8) 0.0229(3) Uani 1 1 d . .
H2 H 0.1648 1.0036 0.3819 0.028 Uiso 1 1 calc R U
C3 C 0.22516(12) 1.20490(17) 0.39792(8) 0.0235(3) Uani 1 1 d . .
H3 H 0.1638 1.2391 0.4192 0.028 Uiso 1 1 calc R U
C4 C 0.31342(12) 1.29514(16) 0.38781(8) 0.0220(3) Uani 1 1 d . .
C5 C 0.40422(11) 1.24217(16) 0.35767(7) 0.0206(3) Uani 1 1 d . .
C6 C 0.40943(11) 1.09961(16) 0.33869(7) 0.0193(3) Uani 1 1 d . .
C7 C 0.51147(12) 1.04695(17) 0.30873(8) 0.0240(3) Uani 1 1 d . .
H7A H 0.5388 1.1246 0.2807 0.029 Uiso 1 1 calc R U
H7B H 0.4848 0.9681 0.2739 0.029 Uiso 1 1 calc R U
C8 C 0.61510(13) 0.99482(18) 0.36941(9) 0.0302(4) Uani 1 1 d . .
H8A H 0.6875 1.0059 0.3507 0.036 Uiso 1 1 calc R U
H8B H 0.6218 1.0582 0.4127 0.036 Uiso 1 1 calc R U
C9 C 0.60975(13) 0.84243(19) 0.39580(9) 0.0319(4) Uani 1 1 d . .
H9A H 0.6791 0.8246 0.4359 0.038 Uiso 1 1 calc R U
H9B H 0.6147 0.7779 0.3545 0.038 Uiso 1 1 calc R U
C10 C 0.49969(13) 0.80451(18) 0.42418(8) 0.0278(3) Uani 1 1 d . .
H10A H 0.5170 0.7232 0.4586 0.033 Uiso 1 1 calc R U
H10B H 0.4775 0.8862 0.4517 0.033 Uiso 1 1 calc R U
C11 C 0.39945(12) 0.76688(17) 0.36192(8) 0.0244(3) Uani 1 1 d . .
H11 H 0.3938 0.6709 0.3459 0.029 Uiso 1 1 calc R U
C12 C 0.31763(12) 0.85636(16) 0.32716(7) 0.0208(3) Uani 1 1 d . .
C13 C 0.22890(11) 0.81073(17) 0.26054(7) 0.0208(3) Uani 1 1 d . .
C14 C 0.19055(12) 0.90844(16) 0.20426(8) 0.0212(3) Uani 1 1 d . .
H14 H 0.2106 1.0058 0.2117 0.025 Uiso 1 1 calc R U
C15 C 0.12263(12) 0.86321(17) 0.13695(8) 0.0210(3) Uani 1 1 d . .
C16 C 0.09067(11) 0.72124(16) 0.12634(7) 0.0203(3) Uani 1 1 d . .
C17 C 0.12217(12) 0.62547(16) 0.18445(8) 0.0208(3) Uani 1 1 d . .
C18 C 0.19211(12) 0.66960(16) 0.25140(8) 0.0225(3) Uani 1 1 d . .
H18 H 0.2147 0.6038 0.2907 0.027 Uiso 1 1 calc R U
C19 C 0.23275(15) 1.4928(2) 0.43966(10) 0.0363(4) Uani 1 1 d . .
H19A H 0.2443 1.5953 0.4469 0.054 Uiso 1 1 calc R U
H19B H 0.1543 1.4748 0.4100 0.054 Uiso 1 1 calc R U
H19C H 0.2414 1.4461 0.4877 0.054 Uiso 1 1 calc R U
C20 C 0.56996(14) 1.3882(2) 0.40284(10) 0.0346(4) Uani 1 1 d . .
H20A H 0.6235 1.4531 0.3855 0.052 Uiso 1 1 calc R U
H20B H 0.5298 1.4390 0.4362 0.052 Uiso 1 1 calc R U
H20C H 0.6142 1.3086 0.4292 0.052 Uiso 1 1 calc R U
C21 C 0.09476(15) 1.09863(18) 0.08926(9) 0.0315(4) Uani 1 1 d . .
H21A H 0.0658 1.1486 0.0426 0.047 Uiso 1 1 calc R U
H21B H 0.0481 1.1259 0.1249 0.047 Uiso 1 1 calc R U
H21C H 0.1766 1.1241 0.1088 0.047 Uiso 1 1 calc R U
C22 C 0.09630(13) 0.63066(18) 0.00954(8) 0.0277(4) Uani 1 1 d . .
H22A H 0.0461 0.6005 -0.0373 0.042 Uiso 1 1 calc R U
H22B H 0.1463 0.7090 0.0005 0.042 Uiso 1 1 calc R U
H22C H 0.1451 0.5509 0.0317 0.042 Uiso 1 1 calc R U
C23 C 0.10233(17) 0.39316(18) 0.23068(9) 0.0361(4) Uani 1 1 d . .
H23A H 0.0700 0.3000 0.2139 0.054 Uiso 1 1 calc R U
H23B H 0.1865 0.3844 0.2505 0.054 Uiso 1 1 calc R U
H23C H 0.0645 0.4288 0.2693 0.054 Uiso 1 1 calc R U
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'
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
C4 O1 C19 117.05(13)
C5 O2 C20 115.76(12)
C15 O3 C21 117.25(12)
C16 O4 C22 112.51(10)
C17 O5 C23 116.68(12)
C2 C1 C6 119.28(14)
C2 C1 C12 120.02(13)
C6 C1 C12 120.69(12)
C3 C2 C1 121.86(13)
C2 C3 C4 119.33(13)
O1 C4 C3 124.69(13)
O1 C4 C5 115.74(13)
C3 C4 C5 119.51(14)
O2 C5 C6 119.14(12)
O2 C5 C4 119.07(14)
C6 C5 C4 121.62(13)
C5 C6 C1 118.33(12)
C5 C6 C7 119.47(13)
C1 C6 C7 122.20(14)
C6 C7 C8 113.40(12)
C9 C8 C7 116.92(13)
C8 C9 C10 115.17(13)
C11 C10 C9 111.52(13)
C12 C11 C10 125.74(15)
C11 C12 C1 121.55(13)
C11 C12 C13 121.10(14)
C1 C12 C13 117.06(12)
C14 C13 C18 119.84(13)
C14 C13 C12 118.93(13)
C18 C13 C12 121.00(13)
C13 C14 C15 119.92(14)
O3 C15 C16 115.38(12)
O3 C15 C14 124.30(14)
C16 C15 C14 120.30(14)
O4 C16 C15 119.85(13)
O4 C16 C17 120.45(13)
C15 C16 C17 119.67(12)
O5 C17 C16 115.50(12)
O5 C17 C18 124.35(13)
C16 C17 C18 120.14(14)
C17 C18 C13 119.88(14)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O1 C4 1.3749(19)
O1 C19 1.4217(19)
O2 C5 1.3859(17)
O2 C20 1.426(2)
O3 C15 1.3706(18)
O3 C21 1.4221(19)
O4 C16 1.3838(16)
O4 C22 1.4353(17)
O5 C17 1.3686(18)
O5 C23 1.428(2)
C1 C2 1.390(2)
C1 C6 1.410(2)
C1 C12 1.492(2)
C2 C3 1.384(2)
C3 C4 1.384(2)
C4 C5 1.399(2)
C5 C6 1.394(2)
C6 C7 1.5094(19)
C7 C8 1.547(2)
C8 C9 1.523(2)
C9 C10 1.539(2)
C10 C11 1.5015(19)
C11 C12 1.334(2)
C12 C13 1.4964(19)
C13 C14 1.392(2)
C13 C18 1.397(2)
C14 C15 1.3947(19)
C15 C16 1.392(2)
C16 C17 1.393(2)
C17 C18 1.3957(19)
