#------------------------------------------------------------------------------
#$Date: 2019-11-26 06:27:54 +0200 (Tue, 26 Nov 2019) $
#$Revision: 242825 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/13/29/4132965.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_4132965
loop_
_publ_author_name
'Li, Quan'
'Qian, Hai'
'Shao, Baihao'
'Hughes, Russell P.'
'Aprahamian, Ivan'
_publ_section_title
;
 Building Strain with Large Macrocycles and Using It To Tune the Thermal
 Half-Lives of Hydrazone Photochromes.
;
_journal_issue                   37
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              11829
_journal_page_last               11835
_journal_paper_doi               10.1021/jacs.8b07612
_journal_volume                  140
_journal_year                    2018
_chemical_absolute_configuration unk
_chemical_formula_moiety         'C19 H18 N2 O4, 0.125(C2 H6 O)'
_chemical_formula_sum            'C19.25 H18.75 N2 O4.125'
_chemical_formula_weight         344.11
_space_group_crystal_system      orthorhombic
_space_group_IT_number           45
_space_group_name_Hall           'I 2 -2c'
_space_group_name_H-M_alt        'I b a 2'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_audit_creation_date             2017-04-10
_audit_creation_method
;
Olex2 1.2-alpha
(compiled 2017.03.28 svn.r3405 for OlexSys, GUI svn.r5335)
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   21.8904(4)
_cell_length_b                   22.9870(4)
_cell_length_c                   6.91370(10)
_cell_measurement_reflns_used    2659
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      72.07
_cell_measurement_theta_min      2.79
_cell_volume                     3478.94(10)
_computing_cell_refinement       'SAINT v8.34A (Bruker, 2013)'
_computing_data_collection       'COSMO (BRUKER, V1.61, 2009)'
_computing_data_reduction        'SAINT v8.34A (Bruker, 2013)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      173(2)
_diffrn_detector_area_resol_mean 8.36
_diffrn_measured_fraction_theta_full 0.989
_diffrn_measured_fraction_theta_max 0.983
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0581
_diffrn_reflns_av_unetI/netI     0.0423
_diffrn_reflns_Laue_measured_fraction_full 0.989
_diffrn_reflns_Laue_measured_fraction_max 0.983
_diffrn_reflns_limit_h_max       27
_diffrn_reflns_limit_h_min       -26
_diffrn_reflns_limit_k_max       27
_diffrn_reflns_limit_k_min       -27
_diffrn_reflns_limit_l_max       6
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_number            10378
_diffrn_reflns_point_group_measured_fraction_full 0.991
_diffrn_reflns_point_group_measured_fraction_max 0.986
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         72.172
_diffrn_reflns_theta_min         2.787
_diffrn_source                   'sealed tube'
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.769
_exptl_absorpt_correction_T_max  0.7536
_exptl_absorpt_correction_T_min  0.6365
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2012/1 (Bruker,2012) was used for absorption correction. wR2(int) was 0.0693 before and 0.0618 after correction. The Ratio of minimum to maximum transmission is 0.8446. The λ/2 correction factor is 0.0015.'
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.314
_exptl_crystal_description       needle
_exptl_crystal_F_000             1450
_exptl_crystal_recrystallization_method 'used as received'
_exptl_crystal_size_max          0.141
_exptl_crystal_size_mid          0.095
_exptl_crystal_size_min          0.078
_refine_diff_density_max         0.703
_refine_diff_density_min         -0.248
_refine_diff_density_rms         0.085
_refine_ls_abs_structure_details
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   -0.3(6)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.084
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     235
_refine_ls_number_reflns         2655
_refine_ls_number_restraints     3
_refine_ls_restrained_S_all      1.084
_refine_ls_R_factor_all          0.0679
_refine_ls_R_factor_gt           0.0552
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.1149P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1633
_refine_ls_wR_factor_ref         0.1734
_reflns_Friedel_coverage         0.838
_reflns_Friedel_fraction_full    0.994
_reflns_Friedel_fraction_max     0.990
_reflns_number_gt                2191
_reflns_number_total             2655
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            ja8b07612_si_005.cif
_cod_data_source_block           ia417a
_cod_database_code               4132965
_shelxl_version_number           2014/6
_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.
;
_shelx_estimated_absorpt_t_max   0.942
_shelx_estimated_absorpt_t_min   0.899
_olex2_refinement_description
;
1. Twinned data refinement
 Scales: 1.3(6)
 -0.3(6)
2. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups, All O(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
3. Restrained distances
 C1S-O1S
 1.48 with sigma of 0.02
 C2S-C1S
 1.54 with sigma of 0.02
4. Others
 Fixed Sof: O1S(0.125) H1S(0.125) C1S(0.125) H1SB(0.125) H1SA(0.125)
 C2S(0.125) H2SA(0.125) H2SC(0.125) H2SB(0.125)
5.a Riding coordinates:
 O1S(H1S), C1S(H1SB,H1SA), C2S(H2SA,H2SC,H2SB)
5.b Secondary CH2 refined with riding coordinates:
 C3(H3A,H3B), C4(H4A,H4B), C5(H5A,H5B), C6(H6A,H6B)
5.c Aromatic/amide H refined with riding coordinates:
 N2(H2), C10(H10), C11(H11), C12(H12), C13(H13), C15(H15), C16(H16), C17(H17),
 C18(H18), C19(H19)
;
_olex2_diffrn_ambient_temperature_device 'Oxford Cryosystems'
_olex2_exptl_crystal_mounting_method
'The crystal was mounted on a nylon loop with paratone oil'
_olex2_submission_original_sample_id 1q-279-C4
_olex2_submission_special_instructions 'No special instructions were received'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, z'
'x+1/2, -y+1/2, z'
'-x+1/2, y+1/2, z'
'x+1/2, y+1/2, z+1/2'
'-x+1/2, -y+1/2, z+1/2'
'x+1, -y+1, z+1/2'
'-x+1, y+1, 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
O1 O 0.80853(13) 0.65839(11) 0.5476(5) 0.0349(7) Uani 1 1 d . . .
N1 N 0.70410(15) 0.58725(14) 0.4911(5) 0.0312(7) Uani 1 1 d . . .
C1 C 0.70384(19) 0.64318(16) 0.4813(6) 0.0310(8) Uani 1 1 d . . .
O2 O 0.75673(15) 0.73113(13) 0.4069(6) 0.0431(8) Uani 1 1 d . . .
N2 N 0.75546(15) 0.55573(13) 0.4991(6) 0.0315(7) Uani 1 1 d . . .
H2 H 0.7914 0.5728 0.5047 0.038 Uiso 1 1 calc R . .
C2 C 0.75809(18) 0.68266(17) 0.4735(6) 0.0313(9) Uani 1 1 d . . .
O3 O 0.87532(13) 0.53664(12) 0.5130(5) 0.0370(7) Uani 1 1 d . . .
C3 C 0.8610(2) 0.69733(19) 0.5707(7) 0.0383(10) Uani 1 1 d . . .
H3A H 0.8527 0.7265 0.6729 0.046 Uiso 1 1 calc R . .
H3B H 0.8694 0.7181 0.4482 0.046 Uiso 1 1 calc R . .
O4 O 0.91091(14) 0.44561(13) 0.5264(6) 0.0465(8) Uani 1 1 d . . .
C4 C 0.9149(2) 0.65966(19) 0.6266(7) 0.0382(10) Uani 1 1 d . . .
H4A H 0.9030 0.6346 0.7368 0.046 Uiso 1 1 calc R . .
H4B H 0.9487 0.6851 0.6707 0.046 Uiso 1 1 calc R . .
C5 C 0.9385(2) 0.62060(19) 0.4602(7) 0.0403(10) Uani 1 1 d . . .
H5A H 0.9128 0.6275 0.3446 0.048 Uiso 1 1 calc R . .
H5B H 0.9807 0.6327 0.4275 0.048 Uiso 1 1 calc R . .
C6 C 0.93872(18) 0.55645(19) 0.5030(8) 0.0392(9) Uani 1 1 d . . .
H6A H 0.9608 0.5352 0.3999 0.047 Uiso 1 1 calc R . .
H6B H 0.9596 0.5490 0.6276 0.047 Uiso 1 1 calc R . .
C7 C 0.86771(19) 0.47902(16) 0.5192(6) 0.0335(8) Uani 1 1 d . . .
C8 C 0.80325(19) 0.45952(16) 0.5119(6) 0.0308(8) Uani 1 1 d . . .
C9 C 0.75074(19) 0.49573(17) 0.4983(6) 0.0306(8) Uani 1 1 d . . .
C10 C 0.6935(2) 0.46953(18) 0.4801(8) 0.0377(9) Uani 1 1 d . . .
H10 H 0.6581 0.4932 0.4682 0.045 Uiso 1 1 calc R . .
C11 C 0.6874(2) 0.40964(19) 0.4791(7) 0.0413(10) Uani 1 1 d . . .
H11 H 0.6480 0.3929 0.4655 0.050 Uiso 1 1 calc R . .
C12 C 0.7380(2) 0.37357(18) 0.4977(8) 0.0438(11) Uani 1 1 d . . .
H12 H 0.7334 0.3325 0.4992 0.053 Uiso 1 1 calc R . .
C13 C 0.7945(2) 0.39846(17) 0.5137(6) 0.0380(9) Uani 1 1 d . . .
H13 H 0.8292 0.3739 0.5266 0.046 Uiso 1 1 calc R . .
C14 C 0.64266(19) 0.67071(18) 0.4708(6) 0.0337(9) Uani 1 1 d . . .
C15 C 0.6314(2) 0.72583(18) 0.5519(7) 0.0369(9) Uani 1 1 d . . .
H15 H 0.6635 0.7467 0.6130 0.044 Uiso 1 1 calc R . .
C16 C 0.5729(2) 0.7497(2) 0.5422(8) 0.0444(11) Uani 1 1 d . . .
H16 H 0.5653 0.7866 0.5987 0.053 Uiso 1 1 calc R . .
C17 C 0.5264(2) 0.7205(2) 0.4522(8) 0.0460(12) Uani 1 1 d . . .
H17 H 0.4869 0.7375 0.4449 0.055 Uiso 1 1 calc R . .
C18 C 0.5368(2) 0.6662(2) 0.3718(8) 0.0475(12) Uani 1 1 d . . .
H18 H 0.5044 0.6459 0.3103 0.057 Uiso 1 1 calc R . .
C19 C 0.5944(2) 0.6412(2) 0.3806(7) 0.0421(11) Uani 1 1 d . . .
H19 H 0.6012 0.6039 0.3254 0.050 Uiso 1 1 calc R . .
O1S O 0.5000 0.5000 -0.004(7) 0.147(18) Uiso 0.25 2 d DS T P
H1S H 0.5084 0.5284 -0.1002 0.177 Uiso 0.125 1 d R . .
C1S C 0.522(2) 0.496(2) 0.196(6) 0.056(11) Uiso 0.125 1 d D . .
H1SB H 0.5490 0.4634 0.1906 0.067 Uiso 0.125 1 d R . .
H1SA H 0.5479 0.5298 0.1906 0.067 Uiso 0.125 1 d R . .
C2S C 0.5000 0.5000 0.405(7) 0.089(14) Uiso 0.25 2 d DS T P
H2SA H 0.5341 0.5005 0.4921 0.133 Uiso 0.125 1 d R . .
H2SC H 0.4750 0.5337 0.4266 0.133 Uiso 0.125 1 d R . .
H2SB H 0.4762 0.4655 0.4266 0.133 Uiso 0.125 1 d R . .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 '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_
_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
C2 O1 C3 115.7(3) . .
C1 N1 N2 123.1(3) . .
N1 C1 C2 127.2(4) . .
N1 C1 C14 115.6(4) . .
C14 C1 C2 117.1(3) . .
N1 N2 H2 120.8 . .
N1 N2 C9 118.5(3) . .
C9 N2 H2 120.8 . .
O1 C2 C1 112.8(3) . .
O2 C2 O1 123.5(4) . .
O2 C2 C1 123.7(4) . .
C7 O3 C6 115.4(3) . .
O1 C3 H3A 110.4 . .
O1 C3 H3B 110.4 . .
O1 C3 C4 106.8(3) . .
H3A C3 H3B 108.6 . .
C4 C3 H3A 110.4 . .
C4 C3 H3B 110.4 . .
C3 C4 H4A 108.8 . .
C3 C4 H4B 108.8 . .
C3 C4 C5 113.7(4) . .
H4A C4 H4B 107.7 . .
C5 C4 H4A 108.8 . .
C5 C4 H4B 108.8 . .
C4 C5 H5A 108.5 . .
C4 C5 H5B 108.5 . .
H5A C5 H5B 107.5 . .
C6 C5 C4 115.0(4) . .
C6 C5 H5A 108.5 . .
C6 C5 H5B 108.5 . .
O3 C6 C5 108.1(3) . .
O3 C6 H6A 110.1 . .
O3 C6 H6B 110.1 . .
C5 C6 H6A 110.1 . .
C5 C6 H6B 110.1 . .
H6A C6 H6B 108.4 . .
O3 C7 C8 114.7(3) . .
O4 C7 O3 122.0(4) . .
O4 C7 C8 123.4(4) . .
C9 C8 C7 126.5(3) . .
C13 C8 C7 115.3(3) . .
C13 C8 C9 118.1(4) . .
N2 C9 C8 121.5(4) . .
N2 C9 C10 119.8(4) . .
C10 C9 C8 118.6(4) . .
C9 C10 H10 119.5 . .
C11 C10 C9 121.0(4) . .
C11 C10 H10 119.5 . .
C10 C11 H11 119.4 . .
C10 C11 C12 121.2(4) . .
C12 C11 H11 119.4 . .
C11 C12 H12 120.7 . .
C13 C12 C11 118.6(4) . .
C13 C12 H12 120.7 . .
C8 C13 H13 118.8 . .
C12 C13 C8 122.4(4) . .
C12 C13 H13 118.8 . .
C15 C14 C1 121.6(4) . .
C19 C14 C1 119.7(4) . .
C19 C14 C15 118.8(4) . .
C14 C15 H15 120.1 . .
C16 C15 C14 119.8(4) . .
C16 C15 H15 120.1 . .
C15 C16 H16 119.6 . .
C17 C16 C15 120.8(4) . .
C17 C16 H16 119.6 . .
C16 C17 H17 120.0 . .
C16 C17 C18 120.0(4) . .
C18 C17 H17 120.0 . .
C17 C18 H18 119.8 . .
C17 C18 C19 120.4(5) . .
C19 C18 H18 119.8 . .
C14 C19 H19 119.9 . .
C18 C19 C14 120.3(4) . .
C18 C19 H19 119.9 . .
C1S O1S H1S 133.0 2_665 .
C1S O1S H1S 129.7 . .
C1S O1S C1S 39(4) . 2_665
C2S O1S H1S 45.6 7_454 .
C2S O1S C1S 160.6(18) 7_454 2_665
C2S O1S C1S 160.6(18) 7_454 .
O1S C1S H1SB 102.4 . .
O1S C1S H1SA 96.3 . .
O1S C1S C2S 142(3) . .
C1S C1S O1S 70.6(18) 2_665 .
C1S C1S H1SB 138.7 2_665 .
C1S C1S H1SA 115.8 2_665 .
C1S C1S C2S 71.4(17) 2_665 .
H1SB C1S H1SA 105.3 . .
C2S C1S H1SB 106.0 . .
C2S C1S H1SA 100.1 . .
O1S C2S C1S 161.4(17) 7_455 .
O1S C2S C1S 161.4(17) 7_455 2_665
O1S C2S H2SA 51.0 7_455 .
O1S C2S H2SC 81.0 7_455 .
O1S C2S H2SB 81.0 7_455 .
C1S C2S C1S 37(3) . 2_665
C1S C2S H2SA 110.6 . .
C1S C2S H2SA 147.1 2_665 .
C1S C2S H2SC 85.6 2_665 .
C1S C2S H2SC 112.0 . .
C1S C2S H2SB 105.7 . .
C1S C2S H2SB 91.5 2_665 .
H2SA C2S H2SC 109.5 . .
H2SA C2S H2SB 109.5 . .
H2SC C2S H2SB 109.5 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
O1 C2 1.339(5) .
O1 C3 1.464(5) .
N1 C1 1.287(5) .
N1 N2 1.339(4) .
C1 C2 1.496(5) .
C1 C14 1.483(5) .
O2 C2 1.206(5) .
N2 H2 0.8800 .
N2 C9 1.383(5) .
O3 C6 1.462(5) .
O3 C7 1.336(5) .
C3 H3A 0.9900 .
C3 H3B 0.9900 .
C3 C4 1.515(6) .
O4 C7 1.219(5) .
C4 H4A 0.9900 .
C4 H4B 0.9900 .
C4 C5 1.548(6) .
C5 H5A 0.9900 .
C5 H5B 0.9900 .
C5 C6 1.504(6) .
C6 H6A 0.9900 .
C6 H6B 0.9900 .
C7 C8 1.481(6) .
C8 C9 1.422(6) .
C8 C13 1.417(5) .
C9 C10 1.397(6) .
C10 H10 0.9500 .
C10 C11 1.383(6) .
C11 H11 0.9500 .
C11 C12 1.389(7) .
C12 H12 0.9500 .
C12 C13 1.368(7) .
C13 H13 0.9500 .
C14 C15 1.407(6) .
C14 C19 1.401(6) .
C15 H15 0.9500 .
C15 C16 1.393(6) .
C16 H16 0.9500 .
C16 C17 1.370(7) .
C17 H17 0.9500 .
C17 C18 1.386(7) .
C18 H18 0.9500 .
C18 C19 1.387(7) .
C19 H19 0.9500 .
O1S H1S 0.9500 .
O1S C1S 1.46(2) 2_665
O1S C1S 1.46(2) .
O1S C2S 0.63(4) 7_454
C1S C1S 0.97(9) 2_665
C1S H1SB 0.9604 .
C1S H1SA 0.9602 .
C1S C2S 1.52(2) .
C2S O1S 0.63(4) 7_455
C2S C1S 1.52(2) 2_665
C2S H2SA 0.9599 .
C2S H2SC 0.9600 .
C2S H2SB 0.9599 .
loop_
_twin_individual_id
_twin_individual_mass_fraction_refined
1 1.3(6)
2 -0.3(6)
