#------------------------------------------------------------------------------
#$Date: 2020-06-06 04:11:42 +0300 (Sat, 06 Jun 2020) $
#$Revision: 252959 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/55/82/1558207.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_1558207
loop_
_publ_author_name
'Ding, Xiaodan'
'Unruh, Daniel K.'
'Groeneman , Ryan'
'Hutchins, Kristin M.'
_publ_section_title
;
 Controlling thermal expansion within mixed cocrystals by tuning molecular
 motion capability
;
_journal_name_full               'Chemical Science'
_journal_paper_doi               10.1039/D0SC02795B
_journal_year                    2020
_chemical_formula_sum            'C18 H15.02 N2 O2'
_chemical_formula_weight         291.34
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_cell_setting           triclinic
_symmetry_Int_Tables_number      2
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_audit_creation_date             2020-04-01T17:47:01-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_audit_update_record
;
2020-04-08 deposited with the CCDC.	2020-06-05 downloaded from the CCDC.
;
_cell_angle_alpha                92.5643(9)
_cell_angle_beta                 107.7884(11)
_cell_angle_gamma                114.4264(12)
_cell_formula_units_Z            2
_cell_length_a                   8.15433(11)
_cell_length_b                   9.85391(12)
_cell_length_c                   10.92795(12)
_cell_measurement_reflns_used    17826
_cell_measurement_temperature    230(2)
_cell_measurement_theta_max      77.168
_cell_measurement_theta_min      4.317
_cell_volume                     746.298(19)
_computing_cell_refinement       'CrysAlisPro 1.171.40.65a (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.65a (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.65a (Rigaku OD, 2019)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      230(2)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.974
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0601106
_diffrn_orient_matrix_UB_12      0.0567015
_diffrn_orient_matrix_UB_13      0.1479002
_diffrn_orient_matrix_UB_21      -0.0022293
_diffrn_orient_matrix_UB_22      -0.1527905
_diffrn_orient_matrix_UB_23      0.0268467
_diffrn_orient_matrix_UB_31      0.2137622
_diffrn_orient_matrix_UB_32      0.0641765
_diffrn_orient_matrix_UB_33      0.0145752
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0314
_diffrn_reflns_av_unetI/netI     0.0447
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.974
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            28336
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.974
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         77.38
_diffrn_reflns_theta_min         4.334
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.692
_exptl_absorpt_correction_T_max  1
_exptl_absorpt_correction_T_min  0.83593
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
        CrysAlisPro 1.171.40.65a (Rigaku Oxford Diffraction, 2019)
        Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_density_diffrn    1.298
_exptl_crystal_description       irregular
_exptl_crystal_F_000             307
_exptl_crystal_size_max          0.234
_exptl_crystal_size_mid          0.094
_exptl_crystal_size_min          0.088
_refine_diff_density_max         0.153
_refine_diff_density_min         -0.128
_refine_diff_density_rms         0.028
_refine_ls_extinction_coef       0.0043(7)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.061
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     284
_refine_ls_number_reflns         3095
_refine_ls_number_restraints     567
_refine_ls_restrained_S_all      0.984
_refine_ls_R_factor_all          0.036
_refine_ls_R_factor_gt           0.0336
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0481P)²+0.0823P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0919
_refine_ls_wR_factor_ref         0.0939
_reflns_Friedel_coverage         0
_reflns_number_gt                2836
_reflns_number_total             3095
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d0sc02795b3.cif
_cod_data_source_block           BE50_BA50_230
_cod_original_cell_volume        746.298(17)
_cod_database_code               1558207
_shelx_estimated_absorpt_t_min   0.888
_shelx_estimated_absorpt_t_max   0.956
_shelx_shelxl_version_number     2018/3
loop_
_symmetry_equiv_pos_as_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
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.16744(10) 0.14968(8) 0.30459(7) 0.04860(19) Uani 1 1 d . . . . .
H1 H 0.200304 0.175392 0.385044 0.073 Uiso 1 1 calc R U . . .
O2 O 0.81993(11) 0.22055(10) 0.43230(7) 0.0559(2) Uani 1 1 d . . . . .
H2A H 0.825027 0.257282 0.503991 0.084 Uiso 1 1 calc R U . . .
N1 N 0.26241(13) 0.24357(11) -0.43208(8) 0.0494(2) Uani 1 1 d . . . . .
C1 C 0.31776(14) 0.14865(10) 0.27602(9) 0.0396(2) Uani 1 1 d . . . . .
C2 C 0.49325(14) 0.18396(10) 0.37312(9) 0.0398(2) Uani 1 1 d . . . . .
H2 H 0.509783 0.208476 0.461578 0.048 Uiso 1 1 calc R U . . .
C3 C 0.64496(15) 0.18334(11) 0.34047(9) 0.0429(2) Uani 1 1 d . . . . .
C4 C 0.61940(17) 0.14404(12) 0.20942(10) 0.0500(3) Uani 1 1 d . . . . .
H4 H 0.720336 0.141691 0.186342 0.06 Uiso 1 1 calc R U . . .
C5 C 0.44362(18) 0.10870(12) 0.11432(10) 0.0532(3) Uani 1 1 d . . . . .
H5 H 0.426273 0.08264 0.025908 0.064 Uiso 1 1 calc R U . . .
C6 C 0.29210(16) 0.11046(11) 0.14511(10) 0.0483(2) Uani 1 1 d . . . . .
H6 H 0.173568 0.086223 0.078632 0.058 Uiso 1 1 calc R U . . .
C7 C 0.19719(15) 0.14713(12) -0.35687(10) 0.0484(2) Uani 1 1 d . . . . .
H7 H 0.154713 0.043003 -0.385992 0.058 Uiso 1 1 calc R U . . .
C8 C 0.18898(15) 0.19239(11) -0.23892(10) 0.0459(2) Uani 1 1 d . . . . .
H8 H 0.140844 0.120046 -0.189693 0.055 Uiso 1 1 calc R U . . .
C9 C 0.25232(14) 0.34580(11) -0.19294(9) 0.0421(2) Uani 1 1 d D U . . .
C10 C 0.32586(15) 0.44726(12) -0.26884(11) 0.0491(2) Uani 1 1 d . . . . .
H10 H 0.374576 0.552418 -0.240362 0.059 Uiso 1 1 calc R U . . .
C11 C 0.32627(16) 0.39145(13) -0.38627(11) 0.0514(3) Uani 1 1 d . . . . .
H11 H 0.374209 0.461226 -0.437419 0.062 Uiso 1 1 calc R U . . .
C12A C 0.2199(13) 0.3786(7) -0.0661(7) 0.0363(10) Uani 0.477(3) 1 d D U P A 1
H12A H 0.165795 0.297394 -0.026132 0.044 Uiso 0.477(3) 1 calc R U P A 1
C13A C 0.2663(4) 0.5190(3) -0.0111(3) 0.0342(6) Uani 0.477(3) 1 d D U P A 1
H13A H 0.325045 0.598314 -0.051351 0.041 Uiso 0.477(3) 1 calc R U P A 1
C12B C 0.264(10) 0.453(2) -0.086(4) 0.044(3) Uani 0.033(3) 1 d D U P A 2
H12B H 0.328439 0.557075 -0.086519 0.053 Uiso 0.033(3) 1 calc R U P A 2
C13B C 0.197(6) 0.4215(19) 0.008(4) 0.040(4) Uani 0.033(3) 1 d D U P A 2
H13B H 0.126959 0.317293 0.005877 0.048 Uiso 0.033(3) 1 calc R U P A 2
C14A C 0.2330(12) 0.5621(7) 0.1104(6) 0.0329(10) Uani 0.477(3) 1 d DG U P A 1
C15A C 0.1499(13) 0.4536(6) 0.1783(7) 0.0403(12) Uani 0.477(3) 1 d G U P A 1
H15A H 0.114724 0.350805 0.149655 0.048 Uiso 0.477(3) 1 calc R U P A 1
C16A C 0.1188(14) 0.4973(8) 0.2886(7) 0.0407(13) Uani 0.477(3) 1 d G U P A 1
H16A H 0.062641 0.423897 0.334553 0.049 Uiso 0.477(3) 1 calc R U P A 1
N2A N 0.1709(14) 0.6493(9) 0.3310(7) 0.0395(15) Uani 0.477(3) 1 d G U P A 1
C17A C 0.2540(13) 0.7578(7) 0.2631(7) 0.0391(11) Uani 0.477(3) 1 d G U P A 1
H17A H 0.289203 0.860649 0.291733 0.047 Uiso 0.477(3) 1 calc R U P A 1
C18A C 0.2851(12) 0.7142(6) 0.1528(7) 0.0384(11) Uani 0.477(3) 1 d G U P A 1
H18A H 0.341287 0.78756 0.106834 0.046 Uiso 0.477(3) 1 calc R U P A 1
C14B C 0.2148(12) 0.5268(7) 0.1210(6) 0.0422(12) Uani 0.523(3) 1 d D U P A 2
C15B C 0.1280(13) 0.4432(7) 0.2014(7) 0.0470(11) Uani 0.523(3) 1 d . U P A 2
H15B H 0.079343 0.336869 0.185808 0.056 Uiso 0.523(3) 1 calc R U P A 2
C16B C 0.1139(14) 0.5174(9) 0.3043(8) 0.0468(12) Uani 0.523(3) 1 d . U P A 2
H16B H 0.052587 0.456373 0.355851 0.056 Uiso 0.523(3) 1 calc R U P A 2
N2B N 0.1760(14) 0.6619(9) 0.3375(7) 0.0506(16) Uani 0.523(3) 1 d . U P A 2
C17B C 0.2567(14) 0.7371(8) 0.2613(8) 0.0508(13) Uani 0.523(3) 1 d . U P A 2
H17B H 0.305444 0.843294 0.281919 0.061 Uiso 0.523(3) 1 calc R U P A 2
C18B C 0.2803(11) 0.6820(7) 0.1544(7) 0.0439(11) Uani 0.523(3) 1 d . U P A 2
H18B H 0.339753 0.747874 0.104652 0.053 Uiso 0.523(3) 1 calc R U P A 2
C19 C 0.2487(12) 0.4102(7) -0.0793(7) 0.0475(13) Uani 0.49 1 d D U P A 2
C20 C 0.2370(6) 0.4653(5) 0.0140(4) 0.0502(7) Uani 0.49 1 d D U 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 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
-1 1 2 0.1024
-2 2 -6 0.081
-4 -1 0 0.0438
5 -1 -3 0.0658
1 -6 4 0.0337
4 1 0 0.0468
-2 -4 4 0.0464
-5 0 4 0.0804
-5 1 -1 0.0444
-3 2 -4 0.0582
-1 -5 -1 0.0561
1 5 1 0.0835
5 -3 0 0.0435
-2 6 2 0.0954
4 -6 1 0.0427
0 -6 2 0.0367
-2 -5 3 0.0426
2 4 -3 0.0582
-1 -1 7 0.0957
-4 -2 1 0.0435
-1 6 0 0.0733
-2 4 -5 0.054
4 2 -4 0.0654
-1 5 -4 0.0508
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
C1 O1 H1 109.5 . . ?
C3 O2 H2A 109.5 . . ?
C7 N1 C11 116.84(9) . . ?
O1 C1 C2 121.85(8) . . ?
O1 C1 C6 118.23(9) . . ?
C2 C1 C6 119.92(9) . . ?
C1 C2 C3 120.42(8) . . ?
C1 C2 H2 119.8 . . ?
C3 C2 H2 119.8 . . ?
O2 C3 C2 122.17(8) . . ?
O2 C3 C4 117.99(9) . . ?
C2 C3 C4 119.84(9) . . ?
C5 C4 C3 118.88(10) . . ?
C5 C4 H4 120.6 . . ?
C3 C4 H4 120.6 . . ?
C4 C5 C6 121.95(9) . . ?
C4 C5 H5 119 . . ?
C6 C5 H5 119 . . ?
C5 C6 C1 118.98(10) . . ?
C5 C6 H6 120.5 . . ?
C1 C6 H6 120.5 . . ?
N1 C7 C8 123.31(9) . . ?
N1 C7 H7 118.3 . . ?
C8 C7 H7 118.3 . . ?
C7 C8 C9 119.58(9) . . ?
C7 C8 H8 120.2 . . ?
C9 C8 H8 120.2 . . ?
C19 C9 C10 115.5(3) . . ?
C19 C9 C8 127.2(3) . . ?
C10 C9 C8 117.39(9) . . ?
C19 C9 C12B 15.5(5) . . ?
C10 C9 C12B 100.1(6) . . ?
C8 C9 C12B 142.5(7) . . ?
C10 C9 C12A 128.5(2) . . ?
C8 C9 C12A 114.0(2) . . ?
C11 C10 C9 118.96(10) . . ?
C11 C10 H10 120.5 . . ?
C9 C10 H10 120.5 . . ?
N1 C11 C10 123.87(10) . . ?
N1 C11 H11 118.1 . . ?
C10 C11 H11 118.1 . . ?
C13A C12A C9 121.8(4) . . ?
C13A C12A H12A 119.1 . . ?
C9 C12A H12A 119.1 . . ?
C12A C13A C14A 125.8(4) . . ?
C12A C13A H13A 117.1 . . ?
C14A C13A H13A 117.1 . . ?
C13B C12B C9 128.5(17) . . ?
C13B C12B H12B 115.8 . . ?
C9 C12B H12B 115.8 . . ?
C12B C13B C14B 129.6(15) . . ?
C12B C13B H13B 115.2 . . ?
C14B C13B H13B 115.2 . . ?
C15A C14A C18A 120 . . ?
C15A C14A C13A 121.6(3) . . ?
C18A C14A C13A 118.4(3) . . ?
C14A C15A C16A 120 . . ?
C14A C15A H15A 120 . . ?
C16A C15A H15A 120 . . ?
N2A C16A C15A 120 . . ?
N2A C16A H16A 120 . . ?
C15A C16A H16A 120 . . ?
C16A N2A C17A 120 . . ?
N2A C17A C18A 120 . . ?
N2A C17A H17A 120 . . ?
C18A C17A H17A 120 . . ?
C17A C18A C14A 120 . . ?
C17A C18A H18A 120 . . ?
C14A C18A H18A 120 . . ?
C18B C14B C15B 114.7(3) . . ?
C18B C14B C20 120.6(5) . . ?
C15B C14B C20 124.7(4) . . ?
C18B C14B C13B 135.1(10) . . ?
C15B C14B C13B 109.9(8) . . ?
C20 C14B C13B 15.5(5) . . ?
C16B C15B C14B 119.2(3) . . ?
C16B C15B H15B 120.4 . . ?
C14B C15B H15B 120.4 . . ?
N2B C16B C15B 126.8(3) . . ?
N2B C16B H16B 116.6 . . ?
C15B C16B H16B 116.6 . . ?
C16B N2B C17B 112.7(3) . . ?
N2B C17B C18B 128.2(4) . . ?
N2B C17B H17B 115.9 . . ?
C18B C17B H17B 115.9 . . ?
C17B C18B C14B 118.4(3) . . ?
C17B C18B H18B 120.8 . . ?
C14B C18B H18B 120.8 . . ?
C20 C19 C9 176.6(9) . . ?
C19 C20 C14B 177.6(7) . . ?
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
O1 C1 1.3579(12) . ?
O1 H1 0.83 . ?
O2 C3 1.3552(12) . ?
O2 H2A 0.83 . ?
N1 C7 1.3343(14) . ?
N1 C11 1.3391(14) . ?
C1 C2 1.3864(14) . ?
C1 C6 1.3913(13) . ?
C2 C3 1.3904(14) . ?
C2 H2 0.94 . ?
C3 C4 1.3949(13) . ?
C4 C5 1.3786(16) . ?
C4 H4 0.94 . ?
C5 C6 1.3825(16) . ?
C5 H5 0.94 . ?
C6 H6 0.94 . ?
C7 C8 1.3751(14) . ?
C7 H7 0.94 . ?
C8 C9 1.3900(14) . ?
C8 H8 0.94 . ?
C9 C19 1.383(7) . ?
C9 C10 1.3890(15) . ?
C9 C12B 1.496(19) . ?
C9 C12A 1.533(6) . ?
C10 C11 1.3749(15) . ?
C10 H10 0.94 . ?
C11 H11 0.94 . ?
C12A C13A 1.331(7) . ?
C12A H12A 0.94 . ?
C13A C14A 1.510(5) . ?
C13A H13A 0.94 . ?
C12B C13B 1.298(19) . ?
C12B H12B 0.94 . ?
C13B C14B 1.505(19) . ?
C13B H13B 0.94 . ?
C14A C15A 1.39 . ?
C14A C18A 1.39 . ?
C15A C16A 1.39 . ?
C15A H15A 0.94 . ?
C16A N2A 1.39 . ?
C16A H16A 0.94 . ?
N2A C17A 1.39 . ?
C17A C18A 1.39 . ?
C17A H17A 0.94 . ?
C18A H18A 0.94 . ?
C14B C18B 1.382(5) . ?
C14B C15B 1.383(5) . ?
C14B C20 1.388(6) . ?
C15B C16B 1.373(5) . ?
C15B H15B 0.94 . ?
C16B N2B 1.288(4) . ?
C16B H16B 0.94 . ?
N2B C17B 1.290(4) . ?
C17B C18B 1.366(4) . ?
C17B H17B 0.94 . ?
C18B H18B 0.94 . ?
C19 C20 1.181(8) . ?
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
_geom_hbond_publ_flag
O1 H1 N1 0.83 1.92 2.7466(11) 175.1 1_556 yes
O2 H2A N2A^a 0.83 1.97 2.80(3) 176.7 2_666 yes
O2 H2A N2B^b 0.83 1.88 2.707(6) 177.3 2_666 yes
