#------------------------------------------------------------------------------
#$Date: 2019-11-28 17:33:46 +0100 (jue 28 de nov de 2019) $
#$Revision: 244296 $
#$URL: svn://www.crystallography.net/cod/cif/7/23/86/7238694.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_7238694
loop_
_publ_author_name
'Snape, Timothy J.'
'Karakoula, Katherine'
'Rowther, Farzana'
'Warr, Tracy'
_publ_section_title
;
 Exploiting conformationally restricted
 N,N′-dimethyl-N,N′-diarylureas as biologically active
 CC double bond analogues: synthesis and biological evaluation of
 combretastatin A-4 analogues
;
_journal_issue                   19
_journal_name_full               'RSC Advances'
_journal_page_first              7557
_journal_paper_doi               10.1039/c2ra21096g
_journal_volume                  2
_journal_year                    2012
_chemical_formula_sum            'C18 H22 N2 O5'
_chemical_formula_weight         346.38
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 106.835(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   11.1965(17)
_cell_length_b                   15.030(2)
_cell_length_c                   10.6135(16)
_cell_measurement_reflns_used    1232
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      23.285
_cell_measurement_theta_min      2.691
_cell_volume                     1709.5(4)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0726
_diffrn_reflns_av_sigmaI/netI    0.0787
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            10421
_diffrn_reflns_theta_full        23.25
_diffrn_reflns_theta_max         23.25
_diffrn_reflns_theta_min         1.90
_exptl_absorpt_coefficient_mu    0.099
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            white
_exptl_crystal_density_diffrn    1.346
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             736
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.234
_refine_diff_density_min         -0.245
_refine_diff_density_rms         0.055
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.202
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     231
_refine_ls_number_reflns         2462
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.202
_refine_ls_R_factor_all          0.0980
_refine_ls_R_factor_gt           0.0740
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0350P)²+0.7456P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1243
_refine_ls_wR_factor_ref         0.1329
_reflns_number_gt                1975
_reflns_number_total             2462
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c2ra21096g.txt
_cod_data_source_block           s3173o
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_symmetry_cell_setting' value 'Monoclinic' was changed to
'monoclinic' in accordance with the
/home/saulius/struct/COD-crude-data/automatic-downloads/DataCite-retrospective/RSC/depositions/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 last updated on
2011-04-26.

Automatic conversion script
Id: cif_fix_values 6909 2019-04-08 15:41:33Z antanas 
;
_cod_original_cell_volume        1709.6(4)
_cod_original_sg_symbol_H-M      P2(1)/c
_cod_database_code               7238694
loop_
_symmetry_equiv_pos_as_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
O1 O 0.4790(2) 0.17766(16) 0.4608(2) 0.0145(6) Uani 1 1 d .
O2 O 0.4280(2) 0.06083(16) 0.2636(2) 0.0156(6) Uani 1 1 d .
O3 O 0.5978(2) 0.02401(17) 0.1348(2) 0.0187(7) Uani 1 1 d .
O4 O 0.9070(2) 0.29075(17) 0.5992(3) 0.0175(7) Uani 1 1 d .
O5 O 1.2515(2) 0.37303(17) 0.0770(3) 0.0186(7) Uani 1 1 d .
N1 N 0.8829(3) 0.2400(2) 0.3902(3) 0.0159(8) Uani 1 1 d .
H1 H 0.9201 0.2373 0.3277 0.019 Uiso 1 1 calc R
N2 N 1.0345(3) 0.3432(2) 0.4858(3) 0.0194(8) Uani 1 1 d .
C1 C 0.7708(3) 0.1913(2) 0.3696(4) 0.0132(9) Uani 1 1 d .
C2 C 0.7460(4) 0.1277(2) 0.2702(4) 0.0144(9) Uani 1 1 d .
H2 H 0.8066 0.1147 0.2260 0.017 Uiso 1 1 calc R
C3 C 0.6334(3) 0.0835(3) 0.2360(4) 0.0148(9) Uani 1 1 d .
C4 C 0.5449(3) 0.1004(2) 0.3025(4) 0.0122(9) Uani 1 1 d .
C5 C 0.5717(3) 0.1628(3) 0.4030(4) 0.0157(9) Uani 1 1 d .
C6 C 0.6840(3) 0.2097(3) 0.4366(4) 0.0143(9) Uani 1 1 d .
H6 H 0.7007 0.2535 0.5040 0.017 Uiso 1 1 calc R
C7 C 0.5019(4) 0.2434(3) 0.5627(4) 0.0192(10) Uani 1 1 d .
H7A H 0.5127 0.3017 0.5262 0.029 Uiso 1 1 calc R
H7B H 0.5777 0.2278 0.6326 0.029 Uiso 1 1 calc R
H7C H 0.4310 0.2456 0.5992 0.029 Uiso 1 1 calc R
C8 C 0.4302(4) -0.0317(3) 0.2991(4) 0.0223(10) Uani 1 1 d .
H8A H 0.4818 -0.0648 0.2548 0.033 Uiso 1 1 calc R
H8B H 0.3450 -0.0554 0.2721 0.033 Uiso 1 1 calc R
H8C H 0.4653 -0.0378 0.3946 0.033 Uiso 1 1 calc R
C9 C 0.6793(3) 0.0141(3) 0.0530(4) 0.0178(10) Uani 1 1 d .
H9A H 0.6924 0.0723 0.0174 0.027 Uiso 1 1 calc R
H9B H 0.6414 -0.0267 -0.0196 0.027 Uiso 1 1 calc R
H9C H 0.7596 -0.0100 0.1056 0.027 Uiso 1 1 calc R
C10 C 0.9391(3) 0.2908(3) 0.4980(4) 0.0146(9) Uani 1 1 d .
C11 C 1.1061(4) 0.3952(3) 0.5984(4) 0.0257(11) Uani 1 1 d .
H11A H 1.0709 0.3869 0.6721 0.039 Uiso 1 1 calc R
H11B H 1.1023 0.4583 0.5745 0.039 Uiso 1 1 calc R
H11C H 1.1932 0.3753 0.6245 0.039 Uiso 1 1 calc R
C12 C 1.0796(4) 0.3452(3) 0.3712(4) 0.0158(9) Uani 1 1 d .
C13 C 1.1880(4) 0.3001(3) 0.3742(4) 0.0186(10) Uani 1 1 d .
H13 H 1.2256 0.2621 0.4463 0.022 Uiso 1 1 calc R
C14 C 1.2423(4) 0.3097(3) 0.2730(4) 0.0200(10) Uani 1 1 d .
H14 H 1.3167 0.2785 0.2754 0.024 Uiso 1 1 calc R
C15 C 1.1873(3) 0.3649(3) 0.1689(4) 0.0150(9) Uani 1 1 d .
C16 C 1.0761(3) 0.4074(3) 0.1613(4) 0.0161(9) Uani 1 1 d .
H16 H 1.0363 0.4432 0.0872 0.019 Uiso 1 1 calc R
C17 C 1.0231(4) 0.3969(3) 0.2643(4) 0.0182(10) Uani 1 1 d .
H17 H 0.9467 0.4261 0.2603 0.022 Uiso 1 1 calc R
C18 C 1.2044(4) 0.4328(3) -0.0313(4) 0.0213(10) Uani 1 1 d .
H18A H 1.1200 0.4147 -0.0814 0.032 Uiso 1 1 calc R
H18B H 1.2590 0.4312 -0.0887 0.032 Uiso 1 1 calc R
H18C H 1.2022 0.4934 0.0022 0.032 Uiso 1 1 calc R
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'
N N 0.0061 0.0033 '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
C5 O1 C7 117.2(3)
C4 O2 C8 113.2(3)
C3 O3 C9 116.8(3)
C15 O5 C18 118.6(3)
C10 N1 C1 126.2(3)
C10 N1 H1 116.9
C1 N1 H1 116.9
C10 N2 C12 124.5(3)
C10 N2 C11 119.4(3)
C12 N2 C11 115.8(3)
C6 C1 C2 120.7(4)
C6 C1 N1 122.7(3)
C2 C1 N1 116.5(3)
C3 C2 C1 119.8(4)
C3 C2 H2 120.1
C1 C2 H2 120.1
O3 C3 C2 124.0(3)
O3 C3 C4 115.4(3)
C2 C3 C4 120.6(4)
O2 C4 C5 119.6(3)
O2 C4 C3 121.2(3)
C5 C4 C3 119.0(3)
O1 C5 C4 115.6(3)
O1 C5 C6 123.2(4)
C4 C5 C6 121.1(4)
C1 C6 C5 118.8(4)
C1 C6 H6 120.6
C5 C6 H6 120.6
O1 C7 H7A 109.5
O1 C7 H7B 109.5
H7A C7 H7B 109.5
O1 C7 H7C 109.5
H7A C7 H7C 109.5
H7B C7 H7C 109.5
O2 C8 H8A 109.5
O2 C8 H8B 109.5
H8A C8 H8B 109.5
O2 C8 H8C 109.5
H8A C8 H8C 109.5
H8B C8 H8C 109.5
O3 C9 H9A 109.5
O3 C9 H9B 109.5
H9A C9 H9B 109.5
O3 C9 H9C 109.5
H9A C9 H9C 109.5
H9B C9 H9C 109.5
O4 C10 N2 121.3(4)
O4 C10 N1 123.5(3)
N2 C10 N1 115.2(3)
N2 C11 H11A 109.5
N2 C11 H11B 109.5
H11A C11 H11B 109.5
N2 C11 H11C 109.5
H11A C11 H11C 109.5
H11B C11 H11C 109.5
C17 C12 C13 119.3(4)
C17 C12 N2 121.2(4)
C13 C12 N2 119.3(3)
C12 C13 C14 120.7(4)
C12 C13 H13 119.7
C14 C13 H13 119.7
C15 C14 C13 119.3(4)
C15 C14 H14 120.3
C13 C14 H14 120.3
O5 C15 C14 114.8(3)
O5 C15 C16 124.4(3)
C14 C15 C16 120.8(4)
C15 C16 C17 118.8(4)
C15 C16 H16 120.6
C17 C16 H16 120.6
C12 C17 C16 120.9(4)
C12 C17 H17 119.6
C16 C17 H17 119.6
O5 C18 H18A 109.5
O5 C18 H18B 109.5
H18A C18 H18B 109.5
O5 C18 H18C 109.5
H18A C18 H18C 109.5
H18B C18 H18C 109.5
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O1 C5 1.368(4)
O1 C7 1.433(4)
O2 C4 1.388(4)
O2 C8 1.439(4)
O3 C3 1.365(4)
O3 C9 1.437(4)
O4 C10 1.227(4)
O5 C15 1.374(4)
O5 C18 1.434(4)
N1 C10 1.368(5)
N1 C1 1.414(5)
N1 H1 0.8800
N2 C10 1.364(5)
N2 C12 1.446(5)
N2 C11 1.459(5)
C1 C6 1.388(5)
C1 C2 1.391(5)
C2 C3 1.378(5)
C2 H2 0.9500
C3 C4 1.396(5)
C4 C5 1.387(5)
C5 C6 1.394(5)
C6 H6 0.9500
C7 H7A 0.9800
C7 H7B 0.9800
C7 H7C 0.9800
C8 H8A 0.9800
C8 H8B 0.9800
C8 H8C 0.9800
C9 H9A 0.9800
C9 H9B 0.9800
C9 H9C 0.9800
C11 H11A 0.9800
C11 H11B 0.9800
C11 H11C 0.9800
C12 C17 1.369(5)
C12 C13 1.382(5)
C13 C14 1.387(5)
C13 H13 0.9500
C14 C15 1.376(5)
C14 H14 0.9500
C15 C16 1.381(5)
C16 C17 1.396(5)
C16 H16 0.9500
C17 H17 0.9500
C18 H18A 0.9800
C18 H18B 0.9800
C18 H18C 0.9800
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N1 H1 O4 0.88 2.42 3.211(4) 149.0 4_565
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
C10 N1 C1 C6 20.2(6)
C10 N1 C1 C2 -164.9(4)
C6 C1 C2 C3 1.1(6)
N1 C1 C2 C3 -173.9(3)
C9 O3 C3 C2 -5.9(5)
C9 O3 C3 C4 171.7(3)
C1 C2 C3 O3 175.9(3)
C1 C2 C3 C4 -1.5(5)
C8 O2 C4 C5 -110.0(4)
C8 O2 C4 C3 74.6(4)
O3 C3 C4 O2 -2.0(5)
C2 C3 C4 O2 175.7(3)
O3 C3 C4 C5 -177.3(3)
C2 C3 C4 C5 0.3(5)
C7 O1 C5 C4 -178.4(3)
C7 O1 C5 C6 -1.6(5)
O2 C4 C5 O1 2.7(5)
C3 C4 C5 O1 178.1(3)
O2 C4 C5 C6 -174.2(3)
C3 C4 C5 C6 1.3(5)
C2 C1 C6 C5 0.5(6)
N1 C1 C6 C5 175.2(3)
O1 C5 C6 C1 -178.3(3)
C4 C5 C6 C1 -1.7(5)
C12 N2 C10 O4 178.3(4)
C11 N2 C10 O4 4.7(6)
C12 N2 C10 N1 -2.1(5)
C11 N2 C10 N1 -175.7(3)
C1 N1 C10 O4 10.2(6)
C1 N1 C10 N2 -169.3(3)
C10 N2 C12 C17 84.0(5)
C11 N2 C12 C17 -102.2(4)
C10 N2 C12 C13 -101.6(4)
C11 N2 C12 C13 72.3(5)
C17 C12 C13 C14 2.7(6)
N2 C12 C13 C14 -171.8(3)
C12 C13 C14 C15 0.1(6)
C18 O5 C15 C14 -176.8(3)
C18 O5 C15 C16 3.4(5)
C13 C14 C15 O5 177.1(3)
C13 C14 C15 C16 -3.1(6)
O5 C15 C16 C17 -177.1(3)
C14 C15 C16 C17 3.1(6)
C13 C12 C17 C16 -2.6(6)
N2 C12 C17 C16 171.8(3)
C15 C16 C17 C12 -0.2(6)
