#------------------------------------------------------------------------------
#$Date: 2021-03-05 03:47:02 +0200 (Fri, 05 Mar 2021) $
#$Revision: 262578 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/24/19/7241979.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_7241979
loop_
_publ_author_name
'Pandolfi, Lorenzo'
'Giunchi, Andrea'
'Salzillo, Tommaso'
'Brillante, Aldo'
'Della Valle, Raffaele G.'
'Venuti, Elisabetta'
'Grepioni, Fabrizia'
'D'Agostino, Simone'
_publ_section_title
;
 The impact of solid solution composition on kinetics and mechanism of [2
 + 2] photodimerization of cinnamic acid derivatives
;
_journal_issue                   6
_journal_name_full               CrystEngComm
_journal_page_first              1352
_journal_page_last               1359
_journal_paper_doi               10.1039/D0CE01718C
_journal_volume                  23
_journal_year                    2021
_chemical_formula_moiety         'Br0.75 Cl0.25, C9 H10 N O2'
_chemical_formula_sum            'C9 H10 Br0.75 Cl0.25 N O2'
_chemical_formula_weight         232.97
_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'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2020-06-04
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2020-10-16 deposited with the CCDC.	2020-12-23 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 91.96(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   5.8290(16)
_cell_length_b                   8.757(2)
_cell_length_c                   18.712(8)
_cell_measurement_reflns_used    615
_cell_measurement_temperature    300
_cell_measurement_theta_max      23.1680
_cell_measurement_theta_min      4.0310
_cell_volume                     954.6(5)
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      300
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Xcalibur, Sapphire3'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0600
_diffrn_reflns_av_unetI/netI     0.0955
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       4
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            3394
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        24.998
_diffrn_reflns_theta_max         24.998
_diffrn_reflns_theta_min         3.497
_exptl_absorpt_coefficient_mu    3.295
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.28813
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.46 (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear light yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.621
_exptl_crystal_description       block
_exptl_crystal_F_000             470
_exptl_crystal_size_max          0.05
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.01
_refine_diff_density_max         1.913
_refine_diff_density_min         -1.346
_refine_diff_density_rms         0.172
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.058
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     4
_refine_ls_number_reflns         1678
_refine_ls_number_restraints     4
_refine_ls_restrained_S_all      1.059
_refine_ls_R_factor_all          0.1654
_refine_ls_R_factor_gt           0.1319
_refine_ls_shift/su_max          0.165
_refine_ls_shift/su_mean         0.066
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.1321P)²+14.8779P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.3203
_refine_ls_wR_factor_ref         0.3464
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1153
_reflns_number_total             1678
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d0ce01718c2.cif
_cod_data_source_block           '[1H]Br075Cl025_irrad_2h'
_cod_depositor_comments
'Adding full bibliography for 7241976--7241984.cif.'
_cod_database_code               7241979
_shelx_shelxl_version_number     2016/6
_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.
;
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All N(H,H,H) groups, All O(H) groups
2. Restrained distances
 C9B-O2B
 1.32 with sigma of 0.02
 C9B-O1B
 1.22 with sigma of 0.02
3. Restrained planarity
 C8B, C9B, O1B, O2B
 with sigma of 0.1
 C3B, C4B, C5B, C7B
 with sigma of 0.1
4. Uiso/Uaniso restraints and constraints
Uanis(C1B) = Uanis(C6B) = Uanis(C5B) = Uanis(C4B) = Uanis(C3B) = Uanis(C2B)
Uanis(C7B) = Uanis(C8B) = Uanis(C9B)
Uanis(C1A) = Uanis(C6A) = Uanis(C5A) = Uanis(C4A) = Uanis(C3A) = Uanis(C2A)
5. Others
 Sof(C1B)=Sof(C2B)=Sof(H2B)=Sof(C3B)=Sof(H3B)=Sof(C4B)=Sof(C5B)=Sof(H5B)=
 Sof(C6B)=Sof(H6B)=Sof(C7B)=Sof(H7B)=Sof(C8B)=Sof(H8B)=Sof(C9B)=Sof(N1B)=
 Sof(H1BA)=Sof(H1BB)=Sof(H1BC)=Sof(O1B)=Sof(O2B)=Sof(H2BA)=1-FVAR(1)
 Sof(C1A)=Sof(C2A)=Sof(H2A)=Sof(C3A)=Sof(H3A)=Sof(C4A)=Sof(C5A)=Sof(H5A)=
 Sof(C6A)=Sof(H6A)=Sof(C7A)=Sof(H7A)=Sof(C8A)=Sof(H8A)=Sof(C9A)=Sof(N1A)=
 Sof(H1AA)=Sof(H1AB)=Sof(H1AC)=Sof(O1A)=Sof(O2A)=Sof(H2AA)=FVAR(1)
 Fixed Sof: Br1(0.75) Cl1(0.25)
6.a Everything fixed:
 Br1, Cl1, C1A, C2A, C3A, C4A, C5A, C6A, C7A, C8A, C9A, N1A, O1A, O2A, C1B,
 C2B, C3B, C4B, C5B, C6B, C7B, C8B, C9B, N1B, O1B, O2B
6.b Ternary CH refined with riding coordinates:
 C7B(H7B), C8B(H8B)
6.c Aromatic/amide H refined with riding coordinates:
 C2A(H2A), C3A(H3A), C5A(H5A), C6A(H6A), C7A(H7A), C8A(H8A), C2B(H2B),
 C3B(H3B), C5B(H5B), C6B(H6B)
6.d Tetrahedral OH refined with riding coordinates:
 O2A(H2AA), O2B(H2BA)
6.e Idealised Me refined as rotating group:
 N1A(H1AA,H1AB,H1AC), N1B(H1BA,H1BB,H1BC)
;
_olex2_submission_special_instructions 'No special instructions were received'
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
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Br1 Br 0.898870 0.771320 0.229840 0.054 Uani 0.75 1 d . . P . .
Cl1 Cl 0.900080 0.766870 0.204660 0.012 Uani 0.25 1 d . . P . .
C1A C 0.580980 0.967390 -0.145270 0.044 Uani 0.7397 1 d . . P A 1
C2A C 0.743010 0.966180 -0.089020 0.044 Uani 0.7397 1 d . . P A 1
H2A H 0.874998 1.025342 -0.091488 0.053 Uiso 0.740(19) 1 calc R . P A 1
C3A C 0.707760 0.876540 -0.029080 0.044 Uani 0.7397 1 d . . P A 1
H3A H 0.816155 0.875734 0.008559 0.053 Uiso 0.740(19) 1 calc R . P A 1
C4A C 0.510500 0.788110 -0.025400 0.044 Uani 0.7397 1 d . . P A 1
C5A C 0.348480 0.789310 -0.081650 0.044 Uani 0.7397 1 d . . P A 1
H5A H 0.216503 0.730136 -0.079184 0.053 Uiso 0.740(19) 1 calc R . P A 1
C6A C 0.383720 0.878960 -0.141590 0.044 Uani 0.7397 1 d . . P A 1
H6A H 0.275320 0.879771 -0.179227 0.053 Uiso 0.740(19) 1 calc R . P A 1
C7A C 0.479000 0.702890 0.038850 0.045 Uani 0.7397 1 d . . P A 1
H7A H 0.595378 0.705884 0.074080 0.053 Uiso 0.740(19) 1 calc R . P A 1
C8A C 0.288470 0.617420 0.051600 0.050 Uani 0.7397 1 d . . P A 1
H8A H 0.170615 0.605640 0.017278 0.060 Uiso 0.740(19) 1 calc R . P A 1
C9A C 0.279570 0.546410 0.121040 0.039 Uani 0.7397 1 d . . P A 1
N1A N 0.607570 1.060170 -0.216280 0.057 Uani 0.7397 1 d . . P A 1
H1AA H 0.633093 0.996011 -0.252029 0.086 Uiso 0.740(19) 1 calc GR . P A 1
H1AB H 0.725201 1.124472 -0.211102 0.086 Uiso 0.740(19) 1 calc GR . P A 1
H1AC H 0.479492 1.112634 -0.225972 0.086 Uiso 0.740(19) 1 calc GR . P A 1
O1A O 0.406320 0.578660 0.172570 0.062 Uani 0.7397 1 d . . P A 1
O2A O 0.105120 0.443180 0.129750 0.065 Uani 0.7397 1 d . . P A 1
H2AA H 0.113162 0.408717 0.170504 0.098 Uiso 0.740(19) 1 calc R . P A 1
C1B C 0.582600 0.973110 -0.159450 0.034 Uani 0.2603 1 d . . P A 2
C2B C 0.759770 0.962140 -0.108070 0.034 Uani 0.2603 1 d . . P A 2
H2B H 0.885344 1.027375 -0.109836 0.041 Uiso 0.260(19) 1 calc R . P A 2
C3B C 0.749240 0.853660 -0.054050 0.034 Uani 0.2603 1 d . . P A 2
H3B H 0.867771 0.846319 -0.019674 0.041 Uiso 0.260(19) 1 calc R . P A 2
C4B C 0.561560 0.756160 -0.051410 0.034 Uani 0.2603 1 d . . P A 2
C5B C 0.384400 0.767130 -0.102790 0.034 Uani 0.2603 1 d . . P A 2
H5B H 0.258827 0.701894 -0.101023 0.041 Uiso 0.260(19) 1 calc R . P A 2
C6B C 0.394920 0.875600 -0.156810 0.034 Uani 0.2603 1 d . . P A 2
H6B H 0.276390 0.882934 -0.191186 0.041 Uiso 0.260(19) 1 calc R . P A 2
C7B C 0.560550 0.617980 0.007520 0.048 Uani 0.2603 1 d . . P A 2
H7B H 0.640866 0.649205 0.052011 0.057 Uiso 0.260(19) 1 calc R . P A 2
C8B C 0.328530 0.539240 0.023520 0.048 Uani 0.2603 1 d . . P A 2
H8B H 0.193563 0.578500 -0.003208 0.057 Uiso 0.260(19) 1 calc R . P A 2
C9B C 0.303890 0.521600 0.097630 0.048 Uani 0.2603 1 d D . P A 2
N1B N 0.607600 1.079010 -0.203650 0.051 Uani 0.2603 1 d . . P A 2
H1BA H 0.744432 1.070679 -0.222986 0.077 Uiso 0.260(19) 1 calc GR . P A 2
H1BB H 0.598005 1.168562 -0.181463 0.077 Uiso 0.260(19) 1 calc GR . P A 2
H1BC H 0.498100 1.072923 -0.237860 0.077 Uiso 0.260(19) 1 calc GR . P A 2
O1B O 0.434400 0.546950 0.149240 0.064 Uani 0.2603 1 d D . P A 2
O2B O 0.102470 0.461650 0.111530 0.044 Uani 0.2603 1 d D . P A 2
H2BA H 0.091653 0.452371 0.154891 0.065 Uiso 0.260(19) 1 calc R . P 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'
Br Br -0.2901 2.4595 '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'
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
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2A C1A N1A 124.1 . . ?
C6A C1A C2A 120.0 . . ?
C6A C1A N1A 115.9 . . ?
C1A C2A C3A 120.0 . . ?
C4A C3A C2A 120.0 . . ?
C3A C4A C5A 120.0 . . ?
C3A C4A C7A 117.5 . . ?
C5A C4A C7A 122.4 . . ?
C4A C5A C6A 120.0 . . ?
C1A C6A C5A 120.0 . . ?
C8A C7A C4A 124.1 . . ?
C7A C8A C9A 116.6 . . ?
O1A C9A C8A 124.7 . . ?
O1A C9A O2A 119.1 . . ?
O2A C9A C8A 116.1 . . ?
C6B C1B C2B 120.0 . . ?
N1B C1B C2B 114.0 . . ?
N1B C1B C6B 125.9 . . ?
C3B C2B C1B 120.0 . . ?
C4B C3B C2B 120.0 . . ?
C3B C4B C5B 120.0 . . ?
C3B C4B C7B 119.9 . . ?
C5B C4B C7B 119.8 . . ?
C6B C5B C4B 120.0 . . ?
C5B C6B C1B 120.0 . . ?
C8B C7B C4B 111.9 3_665 . ?
C8B C7B C4B 118.7 . . ?
C8B C7B C8B 93.0 . 3_665 ?
C9B C8B C7B 110.9 . . ?
O1B C9B C8B 132.3 . . ?
O1B C9B O2B 116.6 . . ?
O2B C9B C8B 111.0 . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1A C2A 1.3900 . ?
C1A C6A 1.3900 . ?
C1A N1A 1.5697 . ?
C2A C3A 1.3900 . ?
C3A C4A 1.3900 . ?
C4A C5A 1.3900 . ?
C4A C7A 1.4322 . ?
C5A C6A 1.3901 . ?
C7A C8A 1.3670 . ?
C8A C9A 1.4430 . ?
C9A O1A 1.2275 . ?
C9A O2A 1.3745 . ?
C1B C2B 1.3901 . ?
C1B C6B 1.3900 . ?
C1B N1B 1.2544 . ?
C2B C3B 1.3901 . ?
C3B C4B 1.3900 . ?
C4B C5B 1.3900 . ?
C4B C7B 1.6373 . ?
C5B C6B 1.3900 . ?
C7B C8B 1.5562 . ?
C7B C8B 1.6361 3_665 ?
C8B C9B 1.4075 . ?
C9B O1B 1.2290 . ?
C9B O2B 1.3201 . ?
