#------------------------------------------------------------------------------
#$Date: 2016-08-07 11:19:22 +0300 (Sun, 07 Aug 2016) $
#$Revision: 185212 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/22/52/7225202.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_7225202
loop_
_publ_author_name
'Veerakanellore, Giri Babu'
'Captain, Burjor'
'Ramamurthy, V.'
_publ_section_title
;
 Solid-state photochemistry of cis-cinnamic acids: a competition between
 [2 + 2] addition and cis--trans isomerization
;
_journal_issue                   25
_journal_name_full               CrystEngComm
_journal_page_first              4708
_journal_paper_doi               10.1039/C6CE00682E
_journal_volume                  18
_journal_year                    2016
_chemical_formula_sum            'C22 H26 Br2 O9'
_chemical_formula_weight         594.25
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   mixed
_audit_creation_method           SHELXL-2014/7
_audit_update_record
;
2016-03-10 deposited with the CCDC.
2016-05-11 downloaded from the CCDC.
;
_cell_angle_alpha                108.1410(10)
_cell_angle_beta                 102.7940(10)
_cell_angle_gamma                94.1940(10)
_cell_formula_units_Z            2
_cell_length_a                   9.0513(5)
_cell_length_b                   10.3906(5)
_cell_length_c                   14.5614(7)
_cell_measurement_reflns_used    6033
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      26.93
_cell_measurement_theta_min      2.34
_cell_volume                     1254.09(11)
_computing_cell_refinement       'SAINT+  V8.34A (Bruker, 2015)'
_computing_data_collection       'APEX2 v2.2-0 (Bruker, 2007)'
_computing_data_reduction        'SAINT+  V8.34A (Bruker, 2015)'
_computing_molecular_graphics    'XSHELL v6.3.1 (Bruker, 2004)'
_computing_publication_material  'XCIF v2014/2 (Bruker, 2014)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXS/SHELXTL V6.14 (Bruker, 2015)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker SMART APEX2 CCD diffractometer'
_diffrn_measurement_method       'omega scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0283
_diffrn_reflns_av_unetI/netI     0.0300
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            17137
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.997
_diffrn_reflns_theta_min         1.523
_exptl_absorpt_coefficient_mu    3.279
_exptl_absorpt_correction_T_max  0.7461
_exptl_absorpt_correction_T_min  0.4641
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS 2014/5 Bruker)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.574
_exptl_crystal_description       block
_exptl_crystal_F_000             600
_exptl_crystal_size_max          0.360
_exptl_crystal_size_mid          0.300
_exptl_crystal_size_min          0.080
_refine_diff_density_max         0.767
_refine_diff_density_min         -0.992
_refine_diff_density_rms         0.091
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.031
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     318
_refine_ls_number_reflns         6049
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.031
_refine_ls_R_factor_all          0.0649
_refine_ls_R_factor_gt           0.0482
_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)+(0.0634P)²+1.2012P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1227
_refine_ls_wR_factor_ref         0.1317
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4618
_reflns_number_total             6049
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            c6ce00682e2.cif
_cod_data_source_block           1
_cod_depositor_comments
;
The following automatic conversions were performed:

'_exptl_absorpt_correction_type' value 'Multi-scan' changed to
'multi-scan' according to
/usr/data/users/saulius/crontab/automatic-downloads/rss-feeds/RSC/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 4268 2015-11-12 08:31:59Z antanas 

 Adding full bibliography for 7225194--7225202.cif.
;
_cod_database_code               7225202
_shelx_shelxl_version_number     2014/7
_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   0.385
_shelx_estimated_absorpt_t_max   0.779
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
Br1 Br 0.84409(4) 1.06207(5) 1.18737(2) 0.06362(15) Uani 1 1 d . .
Br2 Br 0.33725(7) 0.68970(5) 1.01976(4) 0.08609(19) Uani 1 1 d . .
O1 O 0.7330(4) 0.9196(3) 0.61133(18) 0.0682(8) Uani 1 1 d . .
O2 O 0.8129(3) 1.1340(2) 0.71099(17) 0.0521(6) Uani 1 1 d . .
H2 H 0.8338 1.1425 0.6610 0.078 Uiso 1 1 calc R U
O3 O 0.8606(3) 0.6165(2) 0.81223(17) 0.0539(6) Uani 1 1 d . .
O4 O 0.3328(3) 0.8574(2) 0.61422(17) 0.0540(6) Uani 1 1 d . .
O5 O 0.4222(3) 1.0787(2) 0.69337(19) 0.0549(6) Uani 1 1 d . .
H5 H 0.3435 1.0883 0.6571 0.082 Uiso 1 1 calc R U
O6 O 0.5399(3) 0.4991(2) 0.63896(19) 0.0605(7) Uani 1 1 d . .
C1 C 0.8107(3) 0.8349(3) 0.8919(2) 0.0346(6) Uani 1 1 d . .
C2 C 0.8585(3) 0.7121(3) 0.9000(2) 0.0436(7) Uani 1 1 d . .
C3 C 0.8983(4) 0.6947(4) 0.9924(3) 0.0582(9) Uani 1 1 d . .
H3 H 0.9288 0.6129 0.9968 0.070 Uiso 1 1 calc R U
C4 C 0.8930(4) 0.7977(4) 1.0778(3) 0.0578(9) Uani 1 1 d . .
H4 H 0.9188 0.7854 1.1397 0.069 Uiso 1 1 calc R U
C5 C 0.8494(3) 0.9180(4) 1.0704(2) 0.0434(7) Uani 1 1 d . .
C6 C 0.8078(3) 0.9376(3) 0.9783(2) 0.0386(6) Uani 1 1 d . .
H6 H 0.7779 1.0201 0.9750 0.046 Uiso 1 1 calc R U
C7 C 0.7556(3) 0.8409(3) 0.78829(19) 0.0324(5) Uani 1 1 d . .
H7 H 0.8225 0.8023 0.7456 0.039 Uiso 1 1 calc R U
C8 C 0.7150(3) 0.9806(3) 0.77994(19) 0.0340(6) Uani 1 1 d . .
H8 H 0.7536 1.0577 0.8427 0.041 Uiso 1 1 calc R U
C9 C 0.7546(3) 1.0071(3) 0.6918(2) 0.0378(6) Uani 1 1 d . .
C10 C 0.8975(7) 0.4861(4) 0.8133(4) 0.0847(15) Uani 1 1 d . .
H10A H 1.0006 0.4969 0.8528 0.127 Uiso 1 1 calc R U
H10B H 0.8888 0.4274 0.7461 0.127 Uiso 1 1 calc R U
H10C H 0.8281 0.4460 0.8416 0.127 Uiso 1 1 calc R U
C11 C 0.5065(3) 0.6765(3) 0.7750(2) 0.0337(5) Uani 1 1 d . .
C12 C 0.4900(4) 0.5350(3) 0.7248(2) 0.0450(7) Uani 1 1 d . .
C13 C 0.4293(5) 0.4424(4) 0.7620(3) 0.0652(10) Uani 1 1 d . .
H13 H 0.4202 0.3489 0.7283 0.078 Uiso 1 1 calc R U
C14 C 0.3822(5) 0.4870(4) 0.8488(3) 0.0644(10) Uani 1 1 d . .
H14 H 0.3410 0.4243 0.8736 0.077 Uiso 1 1 calc R U
C15 C 0.3967(4) 0.6246(3) 0.8980(3) 0.0496(8) Uani 1 1 d . .
C16 C 0.4585(3) 0.7192(3) 0.8620(2) 0.0382(6) Uani 1 1 d . .
H16 H 0.4679 0.8124 0.8968 0.046 Uiso 1 1 calc R U
C17 C 0.5813(3) 0.7762(3) 0.73736(19) 0.0311(5) Uani 1 1 d . .
H17 H 0.5676 0.7342 0.6651 0.037 Uiso 1 1 calc R U
C18 C 0.5428(3) 0.9223(3) 0.75952(19) 0.0311(5) Uani 1 1 d . .
H18 H 0.5127 0.9497 0.8227 0.037 Uiso 1 1 calc R U
C19 C 0.4227(3) 0.9480(3) 0.6807(2) 0.0352(6) Uani 1 1 d . .
C20 C 0.5291(6) 0.3569(4) 0.5845(4) 0.0817(14) Uani 1 1 d . .
H20A H 0.5878 0.3137 0.6266 0.122 Uiso 1 1 calc R U
H20B H 0.5686 0.3467 0.5270 0.122 Uiso 1 1 calc R U
H20C H 0.4238 0.3146 0.5631 0.122 Uiso 1 1 calc R U
C21 C 1.0823(12) 0.5366(11) 0.5933(7) 0.192(6) Uani 1 1 d . .
H21A H 1.1559 0.5313 0.6511 0.230 Uiso 1 1 calc R U
H21B H 1.0626 0.6300 0.6040 0.230 Uiso 1 1 calc R U
C22 C 0.8726(15) 0.5310(18) 0.5095(15) 0.301(11) Uani 1 1 d . .
H22A H 0.9086 0.6288 0.5386 0.362 Uiso 1 1 calc R U
H22B H 0.7633 0.5128 0.5025 0.362 Uiso 1 1 calc R U
H31 H 0.199(5) 0.105(5) 0.512(4) 0.073(15) Uiso 1 1 d . .
H32 H 0.108(6) 0.129(5) 0.560(4) 0.072(15) Uiso 1 1 d . .
H33 H 0.921(6) 0.256(5) 0.563(4) 0.073(17) Uiso 1 1 d . .
H34 H 0.831(7) 0.150(6) 0.508(4) 0.098(18) Uiso 1 1 d . .
O11 O 0.1958(4) 0.1223(3) 0.5672(2) 0.0620(7) Uani 1 1 d . .
O12 O 0.8950(3) 0.1920(3) 0.5619(2) 0.0487(6) Uani 1 1 d . .
O13 O 0.9623(11) 0.4511(6) 0.5663(4) 0.198(3) Uani 1 1 d . .
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'
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
_geom_angle_site_symmetry_3
C2 O3 C10 118.4(3) .
C12 O6 C20 118.3(3) .
C6 C1 C2 118.2(3) .
C6 C1 C7 124.5(3) .
C2 C1 C7 117.2(3) .
O3 C2 C3 124.6(3) .
O3 C2 C1 115.0(3) .
C3 C2 C1 120.4(3) .
C4 C3 C2 120.6(3) .
C5 C4 C3 119.1(3) .
C4 C5 C6 121.4(3) .
C4 C5 Br1 119.8(2) .
C6 C5 Br1 118.8(3) .
C1 C6 C5 120.2(3) .
C1 C7 C8 116.9(2) .
C1 C7 C17 113.2(2) .
C8 C7 C17 88.81(19) .
C9 C8 C7 112.3(2) .
C9 C8 C18 113.4(2) .
C7 C8 C18 88.21(19) .
O1 C9 O2 123.5(3) .
O1 C9 C8 123.1(3) .
O2 C9 C8 113.4(2) .
C16 C11 C12 117.8(3) .
C16 C11 C17 121.8(2) .
C12 C11 C17 120.3(3) .
O6 C12 C13 124.3(3) .
O6 C12 C11 115.0(3) .
C13 C12 C11 120.7(3) .
C14 C13 C12 120.6(3) .
C15 C14 C13 119.2(3) .
C14 C15 C16 121.0(3) .
C14 C15 Br2 120.3(3) .
C16 C15 Br2 118.7(2) .
C11 C16 C15 120.7(3) .
C11 C17 C18 120.7(2) .
C11 C17 C7 119.3(2) .
C18 C17 C7 88.19(19) .
C19 C18 C17 117.1(2) .
C19 C18 C8 120.8(2) .
C17 C18 C8 90.6(2) .
O4 C19 O5 123.6(3) .
O4 C19 C18 123.1(3) .
O5 C19 C18 113.3(2) .
O13 C21 C22 92.4(9) 2_766
O13 C22 C21 96.4(8) 2_766
C21 O13 C22 92.6(8) .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Br1 C5 1.898(3) .
Br2 C15 1.903(3) .
O1 C9 1.203(4) .
O2 C9 1.304(4) .
O3 C2 1.358(4) .
O3 C10 1.423(4) .
O4 C19 1.207(4) .
O5 C19 1.313(3) .
O6 C12 1.374(4) .
O6 C20 1.428(4) .
C1 C6 1.380(4) .
C1 C2 1.408(4) .
C1 C7 1.502(4) .
C2 C3 1.384(4) .
C3 C4 1.378(6) .
C4 C5 1.367(5) .
C5 C6 1.392(4) .
C7 C8 1.557(4) .
C7 C17 1.583(4) .
C8 C9 1.503(4) .
C8 C18 1.559(4) .
C11 C16 1.383(4) .
C11 C12 1.403(4) .
C11 C17 1.500(4) .
C12 C13 1.380(5) .
C13 C14 1.376(6) .
C14 C15 1.367(5) .
C15 C16 1.387(4) .
C17 C18 1.533(4) .
C18 C19 1.500(4) .
C21 O13 1.255(9) .
C21 C22 1.599(17) 2_766
C22 O13 1.503(12) .
C22 C21 1.599(17) 2_766
