#------------------------------------------------------------------------------
#$Date: 2016-02-21 02:03:34 +0200 (Sun, 21 Feb 2016) $
#$Revision: 176798 $
#$URL: svn://www.crystallography.net/cod/cif/2/23/47/2234713.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided by IUCr Journals, http://journals.iucr.org/.
#
# The file may be used within the scientific community so long as
# proper attribution is given to the journal article from which the
# data were obtained.
#
data_2234713
loop_
_publ_author_name
'Song, Yong Bin'
'Liu, Bo'
_publ_section_title
;
 3,11-Dibromo-14-(4-chlorophenyl)-14H-dibenzo[a,j]xanthene
 dimethylformamide monosolvate
;
_journal_coeditor_code           LD2054
_journal_issue                   5
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o1460
_journal_paper_doi               10.1107/S1600536812016200
_journal_volume                  68
_journal_year                    2012
_chemical_formula_iupac          'C27 H15 Br2 Cl O, C3 H7 N O'
_chemical_formula_moiety         'C27 H15 Br2 Cl O, C3 H7 N O'
_chemical_formula_sum            'C30 H22 Br2 Cl N O2'
_chemical_formula_weight         623.74
_chemical_name_systematic
;
3,11-Dibromo-14-(4-chlorophenyl)-14H-dibenzo[a,j]xanthene
dimethylformamide monosolvate
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                74.4430(10)
_cell_angle_beta                 80.9670(10)
_cell_angle_gamma                71.4480(10)
_cell_formula_units_Z            2
_cell_length_a                   10.8558(12)
_cell_length_b                   10.9385(12)
_cell_length_c                   11.8946(13)
_cell_measurement_reflns_used    2346
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      23.01
_cell_measurement_theta_min      2.36
_cell_volume                     1286.0(2)
_computing_cell_refinement       'SAINT (Bruker, 2004)'
_computing_data_collection       'SMART (Bruker, 2004)'
_computing_data_reduction        'SAINT (Bruker, 2004)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material  'SHELXTL (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.960
_diffrn_measured_fraction_theta_max 0.960
_diffrn_measurement_device_type  'Bruker SMART 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  0.0248
_diffrn_reflns_av_sigmaI/netI    0.0405
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       12
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       13
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       14
_diffrn_reflns_number            8696
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         2.39
_exptl_absorpt_coefficient_mu    3.285
_exptl_absorpt_correction_T_max  0.518
_exptl_absorpt_correction_T_min  0.415
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 1996)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.611
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             624.0
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.26
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.406
_refine_diff_density_min         -0.524
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.030
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     375
_refine_ls_number_reflns         4522
_refine_ls_number_restraints     55
_refine_ls_restrained_S_all      1.037
_refine_ls_R_factor_all          0.0703
_refine_ls_R_factor_gt           0.0388
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0445P)²+0.0361P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0838
_refine_ls_wR_factor_ref         0.0912
_reflns_number_gt                2902
_reflns_number_total             4522
_reflns_threshold_expression     I>2sigma(I)
_cod_data_source_file            ld2054.cif
_cod_data_source_block           I
_cod_database_code               2234713
_cod_database_fobs_code          2234713
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_disorder_assembly
_atom_site_disorder_group
Br Br1 0.52851(4) 0.29861(5) 0.12824(4) 0.08221(18) Uani d . 1 1 . .
Br Br2 1.12806(5) -0.43299(4) 1.11655(4) 0.08279(18) Uani d . 1 1 . .
Cl Cl1 0.34543(9) 0.24873(11) 0.92900(9) 0.0742(3) Uani d . 1 1 . .
C C1 0.6372(3) 0.2652(4) 0.2508(3) 0.0561(9) Uani d . 1 1 . .
C C2 0.7071(4) 0.3483(4) 0.2477(3) 0.0568(10) Uani d . 1 1 . .
H H2 0.7036 0.4213 0.1850 0.068 Uiso calc R 1 1 . .
C C3 0.6406(3) 0.1539(4) 0.3421(3) 0.0565(9) Uani d . 1 1 . .
H H3 0.5926 0.0973 0.3412 0.068 Uiso calc R 1 1 . .
C C4 0.7150(3) 0.1283(3) 0.4333(3) 0.0508(9) Uani d . 1 1 . .
H H4 0.7166 0.0541 0.4943 0.061 Uiso calc R 1 1 . .
C C5 0.7893(3) 0.2122(3) 0.4366(3) 0.0440(8) Uani d . 1 1 . .
C C6 0.7857(3) 0.3240(3) 0.3399(3) 0.0508(9) Uani d . 1 1 . .
C C7 0.8624(4) 0.4075(4) 0.3393(3) 0.0587(10) Uani d . 1 1 . .
H H7 0.8626 0.4792 0.2761 0.070 Uiso calc R 1 1 . .
C C8 0.9352(4) 0.3849(4) 0.4288(3) 0.0571(10) Uani d . 1 1 . .
H H8 0.9860 0.4400 0.4267 0.068 Uiso calc R 1 1 . .
C C9 0.9339(3) 0.2778(4) 0.5253(3) 0.0507(9) Uani d . 1 1 . .
C C10 0.8637(3) 0.1914(3) 0.5327(3) 0.0443(8) Uani d . 1 1 . .
C C11 0.8579(3) 0.0831(3) 0.6435(3) 0.0438(8) Uani d . 1 1 . .
H H11 0.8662 0.0007 0.6211 0.053 Uiso calc R 1 1 . .
C C12 0.7273(3) 0.1214(3) 0.7159(3) 0.0394(7) Uani d . 1 1 . .
C C13 0.6464(3) 0.0415(3) 0.7511(3) 0.0517(9) Uani d . 1 1 . .
H H13 0.6697 -0.0390 0.7295 0.062 Uiso calc R 1 1 . .
C C14 0.5302(3) 0.0793(4) 0.8187(3) 0.0591(10) Uani d . 1 1 . .
H H14 0.4768 0.0238 0.8432 0.071 Uiso calc R 1 1 . .
C C15 0.4951(3) 0.1983(4) 0.8487(3) 0.0477(8) Uani d . 1 1 . .
C C16 0.5733(3) 0.2804(3) 0.8162(3) 0.0505(9) Uani d . 1 1 . .
H H16 0.5489 0.3611 0.8375 0.061 Uiso calc R 1 1 . .
C C17 0.6901(3) 0.2400(3) 0.7506(3) 0.0480(8) Uani d . 1 1 . .
H H17 0.7448 0.2942 0.7294 0.058 Uiso calc R 1 1 . .
C C18 1.0316(3) 0.1546(3) 0.7020(3) 0.0476(8) Uani d . 1 1 . .
C C19 0.9692(3) 0.0601(3) 0.7161(3) 0.0432(8) Uani d . 1 1 . .
C C20 1.1238(3) 0.1442(4) 0.7777(3) 0.0547(9) Uani d . 1 1 . .
H H20 1.1634 0.2111 0.7652 0.066 Uiso calc R 1 1 . .
C C21 1.1551(3) 0.0378(4) 0.8683(3) 0.0509(9) Uani d . 1 1 . .
H H21 1.2141 0.0331 0.9193 0.061 Uiso calc R 1 1 . .
C C22 1.0987(3) -0.0661(3) 0.8857(3) 0.0449(8) Uani d . 1 1 . .
C C23 1.0052(3) -0.0563(3) 0.8097(3) 0.0441(8) Uani d . 1 1 . .
C C24 1.1331(3) -0.1794(4) 0.9783(3) 0.0517(9) Uani d . 1 1 . .
H H24 1.1934 -0.1859 1.0288 0.062 Uiso calc R 1 1 . .
C C25 1.0783(3) -0.2792(3) 0.9939(3) 0.0520(9) Uani d . 1 1 . .
C C26 0.9516(3) -0.1635(3) 0.8306(3) 0.0486(8) Uani d . 1 1 . .
H H26 0.8905 -0.1592 0.7819 0.058 Uiso calc R 1 1 . .
C C27 0.9868(3) -0.2727(3) 0.9200(3) 0.0529(9) Uani d . 1 1 . .
H H27 0.9504 -0.3419 0.9318 0.063 Uiso calc R 1 1 . .
O O1S 0.2639(19) 0.1711(15) 0.4104(17) 0.146(7) Uani d PDU 0.480(11) 1 A 1
N N1S 0.336(3) 0.321(2) 0.464(3) 0.067(4) Uani d PDU 0.480(11) 1 A 1
C C1S 0.2884(11) 0.2997(12) 0.3778(11) 0.080(3) Uani d PDU 0.480(11) 1 A 1
H H1S 0.2724 0.3592 0.3057 0.096 Uiso calc PR 0.480(11) 1 A 1
C C2S 0.3677(10) 0.2212(13) 0.5620(9) 0.091(4) Uani d PU 0.480(11) 1 A 1
H H2SA 0.2894 0.2086 0.6071 0.136 Uiso calc PR 0.480(11) 1 A 1
H H2SB 0.4180 0.2444 0.6083 0.136 Uiso calc PR 0.480(11) 1 A 1
H H2SC 0.4179 0.1406 0.5394 0.136 Uiso calc PR 0.480(11) 1 A 1
C C3S 0.3956(14) 0.4246(12) 0.4441(14) 0.107(4) Uani d PU 0.480(11) 1 A 1
H H3SA 0.3941 0.4703 0.3630 0.160 Uiso calc PR 0.480(11) 1 A 1
H H3SB 0.4842 0.3873 0.4646 0.160 Uiso calc PR 0.480(11) 1 A 1
H H3SC 0.3485 0.4858 0.4915 0.160 Uiso calc PR 0.480(11) 1 A 1
O O1 1.0076(2) 0.2689(2) 0.6136(2) 0.0576(6) Uani d . 1 1 . .
O O1Q 0.2462(12) 0.226(2) 0.3776(18) 0.174(9) Uani d PDU 0.520(11) 1 A 2
N N1Q 0.349(3) 0.315(3) 0.463(3) 0.070(4) Uani d PDU 0.520(11) 1 A 2
C C1Q 0.3174(14) 0.2003(14) 0.4823(11) 0.128(5) Uani d PDU 0.520(11) 1 A 2
H H1Q 0.3355 0.1260 0.5443 0.153 Uiso calc PR 0.520(11) 1 A 2
C C2Q 0.3047(14) 0.4214(14) 0.3741(10) 0.147(8) Uani d PU 0.520(11) 1 A 2
H H2QA 0.2946 0.3914 0.3082 0.221 Uiso calc PR 0.520(11) 1 A 2
H H2QB 0.3659 0.4722 0.3518 0.221 Uiso calc PR 0.520(11) 1 A 2
H H2QC 0.2220 0.4758 0.3994 0.221 Uiso calc PR 0.520(11) 1 A 2
C C3Q 0.4112(14) 0.336(2) 0.5499(17) 0.196(11) Uani d PU 0.520(11) 1 A 2
H H3QA 0.4956 0.2722 0.5586 0.294 Uiso calc PR 0.520(11) 1 A 2
H H3QB 0.3592 0.3261 0.6231 0.294 Uiso calc PR 0.520(11) 1 A 2
H H3QC 0.4208 0.4239 0.5269 0.294 Uiso calc PR 0.520(11) 1 A 2
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'
Cl Cl 0.1484 0.1585 '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'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
C2 C1 C3 122.1(3)
C2 C1 Br1 120.1(3)
C3 C1 Br1 117.8(3)
C1 C2 C6 119.7(3)
C1 C2 H2 120.1
C6 C2 H2 120.1
C4 C3 C1 119.5(3)
C4 C3 H3 120.2
C1 C3 H3 120.2
C3 C4 C5 121.4(3)
C3 C4 H4 119.3
C5 C4 H4 119.3
C4 C5 C10 122.8(3)
C4 C5 C6 117.4(3)
C10 C5 C6 119.8(3)
C2 C6 C7 121.7(3)
C2 C6 C5 119.7(3)
C7 C6 C5 118.6(3)
C8 C7 C6 121.2(3)
C8 C7 H7 119.4
C6 C7 H7 119.4
C7 C8 C9 119.6(4)
C7 C8 H8 120.2
C9 C8 H8 120.2
C10 C9 O1 122.8(3)
C10 C9 C8 123.1(3)
O1 C9 C8 114.1(3)
C9 C10 C5 117.6(3)
C9 C10 C11 120.8(3)
C5 C10 C11 121.4(3)
C19 C11 C10 109.9(3)
C19 C11 C12 109.9(3)
C10 C11 C12 110.6(3)
C19 C11 H11 108.8
C10 C11 H11 108.8
C12 C11 H11 108.8
C13 C12 C17 117.9(3)
C13 C12 C11 123.0(3)
C17 C12 C11 119.1(3)
C12 C13 C14 120.9(3)
C12 C13 H13 119.5
C14 C13 H13 119.5
C15 C14 C13 119.5(3)
C15 C14 H14 120.3
C13 C14 H14 120.3
C14 C15 C16 121.4(3)
C14 C15 Cl1 119.4(3)
C16 C15 Cl1 119.1(3)
C15 C16 C17 118.3(3)
C15 C16 H16 120.8
C17 C16 H16 120.8
C12 C17 C16 121.9(3)
C12 C17 H17 119.1
C16 C17 H17 119.1
C19 C18 O1 122.8(3)
C19 C18 C20 122.6(3)
O1 C18 C20 114.6(3)
C18 C19 C23 117.5(3)
C18 C19 C11 121.1(3)
C23 C19 C11 121.2(3)
C21 C20 C18 120.5(3)
C21 C20 H20 119.8
C18 C20 H20 119.8
C20 C21 C22 120.2(3)
C20 C21 H21 119.9
C22 C21 H21 119.9
C21 C22 C24 120.7(3)
C21 C22 C23 119.7(3)
C24 C22 C23 119.5(3)
C26 C23 C22 117.6(3)
C26 C23 C19 123.0(3)
C22 C23 C19 119.4(3)
C25 C24 C22 120.2(3)
C25 C24 H24 119.9
C22 C24 H24 119.9
C24 C25 C27 121.5(3)
C24 C25 Br2 119.8(3)
C27 C25 Br2 118.6(3)
C27 C26 C23 122.1(3)
C27 C26 H26 119.0
C23 C26 H26 119.0
C26 C27 C25 119.1(3)
C26 C27 H27 120.4
C25 C27 H27 120.4
C1S N1S C2S 119.2(16)
C1S N1S C3S 121(3)
C2S N1S C3S 116.1(18)
N1S C1S O1S 111.3(17)
N1S C1S H1S 124.3
O1S C1S H1S 124.3
C18 O1 C9 118.2(3)
C2Q N1Q C1Q 123.1(17)
C2Q N1Q C3Q 116.9(19)
C1Q N1Q C3Q 119(2)
N1Q C1Q O1Q 100.8(16)
N1Q C1Q H1Q 129.6
O1Q C1Q H1Q 129.6
N1Q C2Q H2QA 109.5
N1Q C2Q H2QB 109.5
H2QA C2Q H2QB 109.5
N1Q C2Q H2QC 109.5
H2QA C2Q H2QC 109.5
H2QB C2Q H2QC 109.5
N1Q C3Q H3QA 109.5
N1Q C3Q H3QB 109.5
H3QA C3Q H3QB 109.5
N1Q C3Q H3QC 109.5
H3QA C3Q H3QC 109.5
H3QB C3Q H3QC 109.5
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
Br1 C1 1.906(4)
Br2 C25 1.898(3)
Cl1 C15 1.756(3)
C1 C2 1.346(5)
C1 C3 1.392(5)
C2 C6 1.413(5)
C2 H2 0.9300
C3 C4 1.370(5)
C3 H3 0.9300
C4 C5 1.413(4)
C4 H4 0.9300
C5 C10 1.429(4)
C5 C6 1.432(4)
C6 C7 1.416(5)
C7 C8 1.347(5)
C7 H7 0.9300
C8 C9 1.406(5)
C8 H8 0.9300
C9 C10 1.369(4)
C9 O1 1.383(4)
C10 C11 1.527(4)
C11 C19 1.512(4)
C11 C12 1.536(4)
C11 H11 0.9800
C12 C13 1.374(4)
C12 C17 1.384(4)
C13 C14 1.392(5)
C13 H13 0.9300
C14 C15 1.363(5)
C14 H14 0.9300
C15 C16 1.369(4)
C16 C17 1.388(4)
C16 H16 0.9300
C17 H17 0.9300
C18 C19 1.368(4)
C18 O1 1.381(4)
C18 C20 1.408(5)
C19 C23 1.440(4)
C20 C21 1.350(4)
C20 H20 0.9300
C21 C22 1.410(4)
C21 H21 0.9300
C22 C24 1.411(4)
C22 C23 1.424(4)
C23 C26 1.416(4)
C24 C25 1.360(5)
C24 H24 0.9300
C25 C27 1.400(5)
C26 C27 1.363(4)
C26 H26 0.9300
C27 H27 0.9300
O1S C1S 1.453(17)
N1S C1S 1.32(2)
N1S C2S 1.37(3)
N1S C3S 1.42(2)
C1S H1S 0.9300
C2S H2SA 0.9600
C2S H2SB 0.9600
C2S H2SC 0.9600
C3S H3SA 0.9600
C3S H3SB 0.9600
C3S H3SC 0.9600
O1Q C1Q 1.485(18)
N1Q C2Q 1.36(3)
N1Q C1Q 1.36(2)
N1Q C3Q 1.42(2)
C1Q H1Q 0.9300
C2Q H2QA 0.9600
C2Q H2QB 0.9600
C2Q H2QC 0.9600
C3Q H3QA 0.9600
C3Q H3QB 0.9600
C3Q H3QC 0.9600
